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The holidays are one of the most magical times to experience Millerton and the Hudson Valley. From twinkling lights and local markets to festive performances and cozy gatherings, there’s something for everyone — whether you love art, music, shopping, or simply savoring the season with friends and family. Here’s your guide to the best holiday events happening in and around Millerton this year: Photo: lumina at harvest moon Troutbeck Holiday Bazaar Saturday, December 6 (11am–4pm) Sunday, December 7 (10am–2pm) The Troutbeck Holiday Bazaar returns with an extraordinary mix of artisans, boutiques, and designers. You’ll find handcrafted jewelry from Mary MacGill, timeless caftans from two, sustainable fashion by Rentrayage, and so much more — plus plenty of fun for little ones and delicious food options. Members and hotel guests enjoy early access on Saturday from 10–11am. Location: Troutbeck, Amenia, NY Admission: Free with RSVP photo: Craft feast at stissing house Craft Feast 2025 at Stissing House Saturday, December 13 – Sunday, December 14 Join Stissing House — and Deborah Needleman — for the third annual Craft Feast, a weekend celebrating American craft. Fifty makers and dealers will fill the tavern with handmade pottery, baskets, textiles, and more. Expect broth, brooms, whittled spoons, and carols too — it’s as charming and cozy as it sounds. Location: Stissing House, Pine Plains, NY Kids on Stage Presents: A Christmas Carol Saturday, December 13 at 11am & 2pm Sunday, December 14 at 11am This heartwarming musical adaptation of the Dickens classic is performed by young local actors in the Kids on Stage program. Follow Ebenezer Scrooge as he’s visited by ghosts of Christmas Past, Present, and Future — and reminded of the true meaning of the season. Tickets: $10 per person Location: The Center for Performing Arts at Rhinebeck The Polar Express Train Ride – Catskill Mountain Railroad November 14 – December 30 All aboard for a magical journey to the North Pole! The beloved Polar Express experience brings the story to life with hot chocolate, dancing chefs, and a visit from Santa himself. Each child receives a silver sleigh bell — “the first gift of Christmas.” Location: Westbrook Station, Kingston, NY Tickets: Adults $47–56 | Children $37–46 Santa is Coming to Poughkeepsie November 21 – December 24 Capture the magic with Santa photos at the Poughkeepsie Galleria. Walk-ups are welcome every day until closing, and families who book online get extra perks. Location: Poughkeepsie Galleria , Poughkeepsie, NY Red Hook’s 5th Annual Christmas Parade of Lights Saturday, December 13 | Parade starts at 6pm Lineup begins at 4pm at the Red Hook Firehouse . Expect festive floats, food trucks, plenty of lights, and a grand finale with Santa and Mrs. Claus. Location: Downtown Red Hook, NY Naumkeag Winterlights November 28–January 3 | Wednesdays–Sundays, 4:30–9pm A Berkshire favorite, Winterlights transforms Naumkeag’s gardens into a wonderland of sparkling light displays, music, and festive treats. Location: Naumkeag, Stockbridge, MA Lumina: A Magical Light Experience November 21–December 30 | 5–8pm (until 8:30pm Saturdays) Wander through an illuminated forest of over half a million lights at Harvest Moon Farm & Orchard . The glowing trails, holiday music, and family-friendly atmosphere make this a perfect seasonal outing. Location: Harvest Moon Farm & Orchard, North Salem, NY Wonderland of Lights at the Dutchess County Fairgrounds November 28–30, December 4–7 & 18–28 | 5–9pm Drive through hundreds of twinkling light displays set to festive music broadcast right into your car. It’s a classic Hudson Valley holiday tradition that delights kids and adults alike. Location: Dutchess County Fairgrounds , Rhinebeck, NY Holiday Trivia Night at The Stissing Center Saturday, December 6 | 7–9:30pm Test your holiday knowledge with host Alec Sisco at this lively trivia night featuring questions about holiday movies, songs, and traditions. Grab your friends, sip something festive, and join the fun. Location: The Stissing Center , Pine Plains, NY photo: wilderstein historic site Holiday Storytime at Wilderstein Historic Site Saturday, December 13 Families are invited for a cozy morning featuring a reading of A Christmas Carol, hot chocolate, and a tour of the beautifully decorated Wilderstein mansion. Location: Wilderstein Historic Site, Rhinebeck, NY Plan Your Holiday Getaway Whether you’re shopping local, watching a show, or sipping cocoa under the lights, Millerton and its neighboring towns make the holiday season truly special. Stay tuned to Visit Millerton for more festive happenings, winter dining spots, and ways to make the most of this magical time of year.

Get ready for a day of holiday magic in Millerton! The Festival of Lights returns on Friday, November 28 , bringing together neighbors, families, and friends for one of our town’s most beloved traditions. From morning movies to evening carols and the sparkling parade, it’s a full day of festive fun and community cheer. Here’s what’s happening throughout the day: Morning Fun at The Moviehouse Kick off the celebration with a FREE cozy holiday classic at The Moviehouse ! Movie: Arthur Christmas (2011) Doors Open: 9:30 AM Showtime: 10:00 AM Families can enjoy this feel-good favorite together — and every child will receive a free raffle ticket for prizes from local businesses! Raffle at Veterans Park After the movie, head to Veterans Park for the raffle drawing and more festivities. Drawing Time: 12:15 PM Don’t miss your chance to win local gift certificates and Toys — it’s always a crowd favorite! Afternoon Festivities - The fun continues all around town: Cookies and Hot Chocolate from NBT Bank Warm up with complimentary cookies and cocoa at the NBT Bank tent in Veterans Park. From 11:30 AM – 2:30 PM Eggnog, Cookies, and Crafts from Bank of Millbrook Stop by the  Bank of Millbrook  tent in Veterans Park for crafts, eggnog, and cookies. From 11:30 AM – 2:30 PM Cookie Decorating at The NECC Let your creativity shine with festive cookie decorating at the North East Community Center . Time: 12:30 PM – 2:30 PM Woodworking Expo at Irondale Schoolhouse Browse handcrafted works at the Woodworking Expo, running all weekend long. Christmas Parade Porch Party at The Millerton Inn bring your own lawn chairs and blankets and warm up around the fire pit at The Millerton Inn . enjoy hot cocoa, hot toddy's, fried dough, and more on the front porch during the parade of lights. Time: 4:00 pm - 6:00 pm rsvp to 518-592-1900 Millerton's Parade of Lights Evening Magic: Caroling, Parade & Tree Lighting. After the sun sets, Millerton truly shines! Caroling Along Main Street Join in a town-wide singalong — music booklets and candles will be handed out starting at 4:15 PM, with caroling beginning at 4:45 PM. Festival of Lights Parade & Tree Lighting The day ends with Millerton’s most magical moment hosted by The Millerton Fire Company - the Festival of Lights Parade, beginning with the town’s holiday tree lighting. Parade Starts: 5:00 PM Make It a Weekend to Remember The Festival of Lights is Millerton at its best — joyful, welcoming, and full of heart. Whether you’re singing on Main Street, sipping cocoa, or watching the lights twinkle through town, it’s the perfect way to start the holiday season. See you there! #FestivalOfLights #VisitMillerton #HolidayMagic #FamilyFun #SupportLocal #MillertonNY

Photo of the Harlem Valley Rail Trail courtesy of Rich Stalzer Millerton in winter is a haven for those who love crisp outdoor adventures and cozy indoor escapes. Whether you’re looking to embrace the snowy beauty of the season or enjoy a warm, welcoming atmosphere, Millerton has something for everyone. Outdoor Adventures 1. Ski the Slopes Nearby Just a short drive from Millerton, Catamount Mountain Resort and Ski Butternut offer fantastic skiing and snowboarding experiences. Whether you’re hitting the slopes for the first time or are a seasoned skier, these local mountains are perfect for a winter day out. 2. Explore the Harlem Valley Rail Trail Take a peaceful winter walk or snowshoeing adventure along the Rail Trail. The quiet beauty of the snow-covered landscape makes for a refreshing way to enjoy the season. Photo of Taconic State Park 3. Winter Bird Watching Visit serene spots like Rudd Pond to catch glimpses of winter wildlife and hardy birds like cardinals and woodpeckers. 4. Scenic Winter Drives Enjoy the beauty of the countryside with a drive through the rolling hills and frosty farms around Millerton. It’s a picturesque way to take in the season’s charm. Photo of Harney & Sons Tea Shop Indoor Escapes 1. Sip and Savor at Irving Farm and Harney & Sons Tea Shop Cozy up with a rich coffee or latte at Irving Farm Coffee House, or stop by Harney & Sons Tea Shop to sample and shop for a variety of teas perfect for winter sipping. 2. Browse Local Art at Geary Gallery , Mad Rose Gallery , and The Re Institute Millerton’s art scene is thriving in every season. Visit Geary Gallery to enjoy contemporary art exhibits or explore The Re Institute, known for its innovative works in a unique rural setting. Photo of Oblong Books 3. Cozy Up with a Book (or a Puzzle!) from Oblong Books Stop by Oblong Books to find the perfect winter read or pick up a puzzle to tackle on a cold evening. It’s the ideal way to stay entertained and cozy indoors. 4. Catch a Film at The Moviehouse Relax with a movie at the iconic Moviehouse, where you can enjoy the latest films or timeless classics in a warm, inviting setting. Embrace Winter in Millerton From snowy adventures to cozy indoor retreats, Millerton offers plenty of ways to enjoy the winter season. Make the most of your day or weekend in this charming town and experience all it has to offer! #VisitMillerton #WinterAdventures #CozyInMillerton #ExploreDutchessCounty #SupportLocalBusinesses

Photo by Catamount Mountain Resort Winter is a fantastic time to explore the Millerton area with kids! Whether you're looking to stay cozy indoors or head out for a winter adventure, there’s a little something for everyone. Here’s a guide to some top activities in and around Millerton, NY, to make the most of the season with the whole family. 1. Play Indoors at Kids Time When it's too chilly to play outside, head to Kids Time in Millerton, an indoor play space perfect for little ones to run around and explore. With climbing structures, slides, and lots of fun toys, it's an ideal place to burn off energy on a cold winter day. Open on weekends, it’s a great option for a family outing when the weather keeps you indoors. Photo by Trevor Zoo 2. Animal Encounters at Trevor Zoo For a unique winter experience, take a short drive to Trevor Zoo in Millbrook. Kids will love seeing a variety of animals in their cozy enclosures, from red pandas to lemurs. The zoo is small and walkable, making it easy to explore even on chilly days. Plus, the crisp winter air makes it a refreshing outing for families. 3. Explore Local Libraries Millerton and nearby towns offer warm, welcoming libraries with plenty of activities for kids. Millerton's NorthEast-Millerton Library and libraries in surrounding towns often host storytimes, craft events, and reading programs that are perfect for winter days. Check their schedules for special events, or just settle in with a good book in their children’s reading areas. 4. Catch a Movie at The Moviehouse What better way to enjoy a chilly winter afternoon than with a cozy movie? The Moviehouse in Millerton shows family-friendly films, and it’s a great option for kids who love movies and popcorn. It’s also a beautifully restored theater, so the experience feels extra special. Photo by BES 5. Try a Class at BES or Little Red Bird Keep little hands busy with art and activity classes at BES or Little Red Bird in Millerton. Both places offer kids’ classes where they can get creative and make fun crafts, which is a perfect way to bring color to the gray days of winter. Check their schedules for special winter-themed workshops or drop-in times! 6. Tube Down a Nearby Mountain Take advantage of the snow with a tubing trip to a nearby mountain! Catamount Mountain Resort and Mohawk Mountain both offer tubing options that are fun for the whole family. Dress warmly, and get ready for an exhilarating ride down the slopes that kids of all ages will enjoy. Photo of Wethersfield Estate 7. Cross-Country Ski or Snowshoe at Wethersfield Estate For families who love the outdoors, the Wethersfield Estate and Garden offers cross-country skiing and snowshoeing in a beautiful setting. Bring your own gear, and enjoy a peaceful winter adventure through the scenic estate grounds. It’s a great way for kids to try a new activity while experiencing winter’s natural beauty. 8. Warm Up with Hot Chocolate from Candy O’s After an outdoor adventure, warm up with a hot chocolate stop at Candy O’s in Millerton. Known for its sweets and treats, this local shop serves up delicious, creamy hot chocolate that’s sure to be a hit with kids (and parents too). Grab a few treats for the road, and maybe even take a hot chocolate to go for the car ride home. Photo by Wassaic Project 9. Make Art at Wassaic Project 's Weekly Drop-In Check out the Wassaic Project’s weekly family-friendly drop-in art session for a creative twist on the typical weekend activity. Held on Saturdays, this isn’t a drop-off activity but a place where you and your kids can work on fun projects together. It’s an opportunity to connect with local artists, explore creativity, and maybe even bring home some winter-inspired art. 10. Enjoy Nature with Winter Walks Even in winter, Millerton’s natural landscapes are a sight to see. Take a family walk along part of the Harlem Valley Rail Trail , where snow-covered trees and open fields create a peaceful winter wonderland. Millerton and the surrounding area offer endless winter activities for families. From indoor play spaces and art projects to snow-covered trails and hot cocoa, there’s plenty to keep kids entertained and inspired. So bundle up, get out there, and discover everything this season has to offer in Millerton!

Photo of Catamount Mountain Resort Winter in the Hudson Valley brings a whole lot of excitement, especially for those who love skiing and snowboarding. If you’re in Millerton, you’re in the perfect spot to hit some great local slopes. Whether you’re a seasoned snowboarder or just learning to ski, there are fantastic mountains nearby that offer something for everyone. And for those who want a break from the slopes, all three spots have snow tubing, too! Catamount Mountain Resort Location: Hillsdale, NY Only 20 minutes from Millerton, Catamount is a local favorite for both skiers and snowboarders. With a variety of trails ranging from gentle beginner slopes to challenging advanced runs, it's a great mountain for all skill levels. Pro Tips: Night Skiing and Snowboarding: Catamount offers night sessions, giving you the chance to ride under the stars. It’s perfect for squeezing in some extra runs after work or making the most of a weekend trip. Kids Ski or Ride Free: Have young ones just getting started? Kids 6 and under get a free lift ticket, making this a great option for families! Tubing: Don’t miss the tubing park for some extra fun! It’s a great way to enjoy the snow without needing skis or snowboards. Photo of Mohawk Mountain Mohawk Mountain Location: Cornwall, CT Located about 45 minutes away, Mohawk Mountain is another nearby gem for skiing and snowboarding. Known for its well-maintained trails and laid-back atmosphere, it’s a great destination for a relaxed day on the slopes. Pro Tip: Night Skiing and Snowboarding: Mohawk also offers night riding, so you can enjoy a quieter, more peaceful experience. Whether you're skiing or snowboarding, the evening sessions often come with fewer crowds, giving you more space to carve down the mountain. Tubing: In addition to the slopes, Mohawk offers tubing, perfect for families or those looking to switch things up. Photo of Ski Butternut Ski Butternut Location: Great Barrington, MA An hour’s drive from Millerton will take you to Ski Butternut, known for its affordable lift tickets and great terrain for skiing and snowboarding. Whether you're hitting jumps in the terrain park or cruising down wide groomers, there's plenty to enjoy here. Pro Tip: $25 Lift Tickets on Fridays: On non-holiday Fridays, you can score a $25 lift ticket—a huge bargain! Perfect for those looking to get a lot of runs in without breaking the bank. Tubing: Ski Butternut’s tubing area offers fun for all ages, making it a perfect addition to your ski or snowboard day. Which Mountain is Right for You? With three excellent options close to Millerton, it’s just a matter of picking what suits you best: Quickest to Get to: Catamount is your best bet for staying close to town, plus they offer free lift tickets for kids 6 and under. Best for Night Riding: Both Catamount and Mohawk offer night skiing and snowboarding, with Mohawk being known for quieter evening sessions. Best Deal: If you’re looking for an affordable day on the slopes, Ski Butternut’s $25 Friday lift tickets (non-holiday weekends) are unbeatable! All three mountains also offer snow tubing, so whether you want to ski, snowboard, or just slide down a hill, there’s something for everyone. So grab your gear, bring your family or friends, and make the most of winter right here near Millerton! Happy skiing, snowboarding, and tubing!

Photo: Millerton 1887 Millerton may be small — less than a square mile — but this little village has a big story to tell. From railroads and ironworks to art galleries and bookshops, Millerton has reinvented itself time and again. And today, that spirit of creativity and resilience is still alive and well. Born of the Railroad Back in 1851, civil engineer Sidney Miller extended the railroad north, linking Boston to the Hudson River. Practically overnight, a new village sprang up around the tracks — and to honor Miller, they named it Millerton. The railroad transformed the town into a bustling agricultural and commercial hub. Farmers could suddenly send their crops and milk far beyond Dutchess County, while merchants found new customers arriving by train. Hotels soon followed: the Millerton Hotel opened in 1852, George Greathead’s Central Hotel in 1865, and the Brick Block Hotel in 1872. By the time Millerton officially became a village in 1875, it was already known as a lively stop on the map. The Irondale Boom Just down the road, the Millerton Iron Company put the area on the industrial map. Founded in 1854, the Irondale foundry produced up to 12,000 tons of car-wheel pig iron a year by the 1880s. At its height, it employed about 150 people and had its own general store, grist mill, post office, and cemetery (you can still visit the historic marker today). Irondale’s iron fueled the nation’s growth — and gave Millerton its first taste of industry. Peaks and Valleys By the late 1800s, Millerton was thriving, with three railroads converging in the village and three hotels welcoming travelers. But like many small towns, fortunes shifted in the 20th century. Farms closed, the milk plant shut down, and the village quieted. Yet Millerton has always had grit. Over the years, artists, makers, and entrepreneurs have reimagined Main Street, bringing fresh energy to old buildings. A Village with New Life Today, Millerton buzzes with creativity. Independent shops, galleries, and cafés fill downtown. Local favorites like Oblong Books , the Oakhurst Diner , Harney Tea Café , and the Music Cellar give the village its one-of-a-kind character. On Saturdays, the North East Community Center Farmer’s Market is the place to be, with fresh produce, local treats, and neighbors catching up. The NorthEast-Millerton Library hosts art shows, concerts, and community programs, while the weekly Millerton News keeps everyone in the loop. Millerton may look different than it did in the 1800s, but that same spirit of connection and resilience still runs through its streets. Why Visit Millerton? Because here, history isn’t just in the past — it’s woven into everyday life. Whether you’re wandering the historic walking tour, browsing in Oblong Books, or sipping tea on Main Street, you’re part of the next chapter in Millerton’s story. Photo: Millerton Main Street

Photo: Millerton Looking for a getaway that feels worlds away from the city—but only takes a train ride to reach? Millerton, NY, is one of those rare spots where small-town charm meets big flavor. Tucked into the foothills of the Berkshires and just a short ride from the Wassaic train station, Millerton makes for the perfect day trip from NYC. Here’s how to make the most of your visit: Getting There Hop on the Metro-North Harlem Line to Wassaic, the last stop. From there, call Watson Livery —they’ll pick you up and have you in downtown Millerton in less than 20 minutes. Easy, stress-free, and no car required. Breakfast to Start Your Day Fuel up with a hearty breakfast before exploring: Harney Teashop – Sip world-class tea and enjoy fresh-baked goods. Irving Farm Coffee Roasters – A local favorite for strong coffee and a cozy atmosphere. Photo: Irving Farm Coffee Roasters After breakfast, stretch your legs on the scenic Harlem Valley Rail Trail . Whether you’re up for a long bike ride or a short, peaceful walk, this converted rail line offers sweeping views of farmland, forests, and mountains. Lunch at Oakhurst Diner A retro-inspired spot with a modern twist, Oakhurst Diner is perfect for a relaxed lunch. From comfort classics to creative specials, it’s the kind of place that hits the spot every time. A Little Time for You If you have a little extra time before dinner, treat yourself to something special. Pop in for a facial, a blow-out, or a fresh coat of polish at one of Millerton’s salons and spas — it’s the perfect way to unwind between adventures. Explore Millerton’s beauty and wellness spots here. Shop the Village Millerton’s Main Street is lined with independent shops worth exploring. Stop by Oblong Books for a local literary treasure, browse antiques and home goods, and discover boutiques that make it easy to find something unique. Dinner at Willa Cap off your day with a memorable dinner at Willa, where seasonally inspired dishes highlight the best of the Hudson Valley. It’s cozy, delicious, and the perfect place to linger. Photo: Willa End with a Movie Catch a film at The Moviehouse , Millerton’s beloved independent theater. With a mix of blockbusters, indie films, and cultural events, it’s the ideal way to wind down before heading back. Back to the Train When you’re ready to head home, Watson Livery will get you back to Wassaic station in time for your train to NYC. You’ll be home the same evening, with a full day of memories in your back pocket. Millerton makes a wonderful day trip—but don’t be surprised if one day isn’t enough.

Photo of One Cream Studio Whether you're in the mood for a fresh haircut, a relaxing manicure, or a little skincare TLC, Millerton has you covered. These local beauty spots aren’t just places to get pampered—they are places where you can unwind, enjoy a little “me time,” and walk out feeling like your best self. From the warm, welcoming salons to expert care, you'll find the perfect spot to refresh your look and relax. Here’s your guide to the top spots for hair, nails, and beauty treatments in Millerton. Beauty and Skin Care Studios Looking for more than just hair and nails? These beauty spots are all about glowing skin and total relaxation: One Cream Studio Just outside of Millerton, One Cream Studio offers personalized skincare treatments that leave your skin looking and feeling its best. Known for its custom facials and rejuvenating therapies, this studio addresses your skin’s needs in a calming, professional environment. Wildly Lush If you’re looking for a holistic approach to beauty, Wildly Lush is your go-to. This eco-conscious beauty destination offers organic hair and skincare treatments using only the best sustainable products. It’s the perfect place to indulge in a little self-care while staying mindful of your impact on the environment. Hair Salons Looking for a fresh cut or a bold new color? These top-tier salons are ready to work their magic: Hair Modern With a focus on contemporary cuts and creative color, Hair Modern is the go-to spot in Millerton for anyone looking to change their look. The stylists are experts in modern techniques, ensuring you leave feeling stylish and confident. Hylton Hundt Salon Located right in Millerton, Hylton Hundt Salon is known for its warm, inviting vibe and personalized approach to hair care. From precision cuts to gorgeous color treatments, their team is dedicated to creating a look that’s uniquely yours. Mane Street Salon Mane Street Salon offers a laid-back yet professional environment where you can sit back and trust the team to bring your hair goals to life. Whether you’re going for a sleek new cut or a fresh blowout, this Millerton salon will leave you feeling refreshed and fabulous. Salon K A quick stroll through Millerton will take you to Salon K—a full-service salon offering everything from everyday cuts to stunning special event styles. With a focus on making every client feel beautiful and confident, Salon K is perfect for a full-on hair refresh or just a little maintenance. The Hair Lounge by Loren Known for its welcoming atmosphere and exceptional service, The Hair Lounge by Loren in Millerton delivers great results while making you feel right at home. Loren and her team are experts at creating hairstyles that suit your personality and lifestyle, ensuring you leave with a look you love. Nail Salons For a flawless manicure or pedicure, these local nail salons have you covered: Kiki’s Nails Located in the heart of Millerton, Kiki’s Nails is a local favorite for high-quality nail services. This spot is about attention to detail, from simple, clean manicures to intricate nail art. You’ll feel welcomed the second you walk through the door—and leave with perfectly polished nails. New Amore Nail Salon Another gem in Millerton, New Amore Nail Salon, offers a relaxed, friendly atmosphere with services that will leave your hands and feet looking and feeling their best. Whether you’re in the mood for a classic mani-pedi or something more luxurious, New Amore is the perfect place to unwind and pamper yourself. Time to Treat Yourself Millerton has top-notch beauty spots that cater to every need. Whether you're looking for a new cut, a manicure, or a rejuvenating skincare treatment, these local businesses are ready to help you look and feel your best. Now, it’s your turn to book an appointment and treat yourself!

Photo: Soukup Farms Harvest Festival Crisp air, vibrant leaves, and the scent of apple cider—it’s one of the most beautiful times of year in the Hudson Valley and Tri-State region. Whether you’re seeking festive harvest celebrations, spine-tingling haunted attractions, or the perfect weekend for leaf peeping, there’s something for everyone this fall. Fall Festivals & Harvest Celebrations Soukup Farms Harvest Festival – Dover Plains - Every Saturday and Sunday in October Take a scenic hayride to the pumpkin patch, explore the corn maze, and enjoy family activities. Don’t leave without a bottle of their famous maple syrup. Kesicke Farm Fall Festival – Rhinebeck - Every Saturday and Sunday 10am - 5pm from September 20 - October 26, 2025. Enjoy hayrides, a corn maze, pumpkin picking, farm animals, and seasonal treats at this family-friendly farm. Millbrook Vineyards & Winery Harvest Party – Millbrook - October 25 Celebrate the season with wine, live music, and local food vendors. Autumn in the Park - Copake Falls, NY - October 11 Pumpkin Painting, Cornhole, Face Painting, Apples, Kid's Crafts, Photo Opportunities, Booths, Live Animal Show, Hiking, BEAR BUS, Food Truck, and More! Oktoberfest at Rhinebeck – Fairgrounds - October 4 & 5 Handcrafted art, gourmet food, and beer gardens make this event a perfect fall day trip. Little Apple Cidery Celebrations – Hillsdale - October 11 and 12 Celebrate the cidery’s 10th anniversary on October 11, then return on October 12 for Ciderfest XIII, featuring live music, tastings, and seasonal fare. The Incredible Naumkeag Pumpkin Show - Stockbridge, MA - Every Wednesday through Sunday from October 1 - 31 All Children (13 and under) are FREE on Wednesdays and Thursdays from October 1–16 Photo: The Incredible Naumkeag Pumpkin Show Spooky & Haunted Events Haunted Fortress – Stanfordville - October 3rd for four weekends A haunted walk-through experience that’s not for the faint of heart. Forsaken Lands Haunted Attraction – Goshen - Sept 27 for 6 weekends Immerse yourself in a high-intensity haunted trail. The Haunted Mansion – Wappingers Falls - Sept 26 - Nov 1 Classic haunted house thrills in a historic setting. Photo: Haunted Fortress of Stanford Local Trunk-or-Treats Check your town’s Parks & Recreation page for safe, family-friendly trick-or-treat events throughout late October. Murder Mystery Dinner – Millbrook Vineyards & Winery - Sept 26 A night of intrigue, great wine, and delicious food—costumes encouraged. Outdoor Adventures & Leaf Peeping Fall Foliage Half Marathon & 5K – Rhinebeck - October 13 Lace up for a scenic run through peak foliage. Poughkeepsie Regatta – Poughkeepsie - October 4 A full day of rowing competitions along the Hudson River, perfect for a crisp autumn afternoon. Photo: Greig Farm Apple Picking - Check their websites for picking dates Spend the day at Rose Hill Farm or Greig Farm in Red Hook for fresh apples, cider donuts, and farm views. Corn Mazes - Late August through the end of October Navigate your way through the corn maze at The Farm Store in Millerton, Soukup Farms in Dover Plains, or Kesicke Farm in Rhinebeck. Best Time for Leaf Peeping Peak foliage in the Hudson Valley typically runs from late September through mid-October, depending on weather conditions. For the best views: Drive along Route 22 near Millerton for rolling hills and open farmland. Hike the Harlem Valley Rail Trail for a car-free leaf-peeping experience. Visit nearby Bash Bish Falls State Park for a mix of waterfalls and autumn color.

Photo of the Harlem Valley Rail Trail As the air turns crisp and the leaves begin their vibrant transformation, Millerton, NY, becomes a picturesque haven for all things fall. Whether you’re a local or a visitor, there’s no better time to explore the charm of this Hudson Valley gem. From apple picking to scenic hikes, here’s your guide to the best fall activities in and around Millerton. Leaf Peeping Along the Harlem Valley Rail Trail Location : Millerton, NY Highlight : Stunning fall foliage on a scenic trail There’s no better way to take in the beauty of fall than by exploring the Harlem Valley Rail Trail. This scenic path winds through the countryside, offering spectacular views of the changing leaves. Whether you’re walking, biking, or jogging, the trail provides a peaceful escape into nature. The golden yellows, fiery reds, and burnt oranges of the foliage create a breathtaking canopy overhead. For an extra treat, bring along a camera to capture the vibrant colors and tranquil landscapes. Cozy Up with a Chai Latte at Irving Farm Coffee House Location : Millerton, NY Highlight : Warm, seasonal drinks in a welcoming café After a morning of leaf peeping, warm up with a visit to Irving Farm Coffee House. Located in the heart of Millerton, this cozy café is the perfect spot to relax and recharge. Their chai latte, made with a blend of aromatic spices and steamed milk, is the ultimate fall comfort drink. Pair it with one of their freshly baked pastries, and you’ll be ready to tackle whatever the day brings. The friendly atmosphere and charming setting make Irving Farm a must-stop on your fall itinerary. Have Fun in a Corn Maze at The Farm Store at Willow Brook Location : Millerton, NY Highlight : Fresh, local produce, handmade goods, and corn maze For a taste of Millerton’s local flavor, visit The Millerton Farm Store. This charming shop offers a variety of fresh, locally sourced produce, artisanal cheeses, baked goods, and handmade crafts. It's the perfect spot to pick up seasonal ingredients for a cozy fall dinner or to find unique gifts for friends and family. The Farm Store also carries a selection of locally made jams, honey, and other pantry staples, making it a delightful place to explore during your fall outings. Leave some time to check out their corn maze across the street! Photo of Rose Hill Farm Apple Picking at Rose Hill Farm Location : Red Hook, NY Highlight : Organic apple picking in a historic orchard Kick off your fall adventures with a visit to Rose Hill Farm, where apple picking is a cherished tradition. This historic farm offers a variety of organic apples, ready for you to pick straight from the tree. Stroll through the orchard, basket in hand, and savor the crisp, fresh air as you gather your bounty. Rose Hill Farm also offers farm-fresh cider and homemade donuts, perfect for enjoying on a cool fall day. Don’t forget to snap a few photos—the backdrop of colorful autumn leaves makes for stunning memories. Pumpkin Picking and Fall Fun at Kesicke Farm Location : Rhinebeck, NY Highlight : A family-friendly farm with a variety of fall activities Kesicke Farm is an excellent destination for all things fall. You can pick your perfect pumpkin from the patch, take a scenic hayride, and explore the corn maze. The farm also hosts various seasonal events, making it an ideal spot for a day of family-friendly fun. Don’t miss the opportunity to visit the petting zoo and try delicious homemade treats. Visit Big Rock Farm Market Location : Stanfordville, NY Highlight : Farm stand, pumpkin patch, and seasonal activities Big Rock Farm in Stanfordville is another beautiful option for fall activities. Known for its charming farm stand, Big Rock offers a selection of fresh produce, local goods, and, of course, pumpkins. Their pumpkin patch is the perfect place to find your Halloween jack-o'-lantern. The farm also offers seasonal decorations, making it a one-stop shop for all your fall needs. Plan Your Perfect Fall Day in the Hudson Valley Whether leaf-peeping, picking pumpkins, or enjoying a warm chai latte, Millerton and the surrounding areas offer endless opportunities to embrace the beauty of fall. So bundle up in your favorite sweater, grab your friends and family, and head out to explore all this charming region offers. Fall in Millerton is truly a season to remember.

Photo: Silo Bakery The school bell may be ringing, but that doesn’t mean the summer fun has to stop. As routines ramp up with early mornings, packed lunches, practices, and homework, it’s easy to feel like the sparkle of summer fades too quickly. But here in the Hudson Valley, Northwest Connecticut, and nearby corners of the Berkshires, the magic of summer can linger well into September and beyond. Whether it’s a quick stop at a favorite bakery, a post-dinner ice cream run, or a lazy Sunday spent exploring the outdoors, here are some easy ways to keep that carefree summer energy going—even when backpacks and sports schedules take over. Keep It Simple After School Back to school doesn’t have to mean back to boring. A short walk or a spontaneous treat can do wonders to shake off a long day. Sweet Stops: Grab a cookie or tea latte from Irving Farm or browse the blends at the Harney & Sons Tea Shop . Pick up a box of donuts from Candy O’s , a chocolate croissant at Silo Bakery in Amenia, or some decadent bites from Vitsky Bakery in Wassaic. The Ancram Little Store is also great for quick snacks and warm vibes. Library Visits: Local libraries are the perfect spot to spark imagination after a structured day. Check out the Amenia Free Library , NorthEast-Millerton Library , or the Hotchkiss Library of Sharon . After-Dinner Ice Cream Run? Always Yes. There’s no rule that says ice cream is only for summer. Try: Candy O’s (Millerton) Grasslands (Pine Plains) Fudgy’s Ice Cream (Amenia) Kelly’s Creamery (Dover Plains) Bonus: Caddie Shack (North Canaan) has a mini golf course and batting cages next to their ice cream shop—perfect for getting the wiggles out after a long day sitting still. Photo: Kelly's Creamery Make Space for Nature There’s something grounding about being in nature, especially when routines start to feel chaotic. Hike or bike the Harlem Valley Rail Trail . Visit the Farm Store for goats, goodies, and their seasonal corn maze. Head to Eddie Collins Park , the Stanford Recreation Area , or Freedom Park in Millbrook. Cast a Line (and a Little Peace) Fishing is a great way to slow down and connect with the world around you. These local spots are perfect for kids and adults alike: Rudd Pond (Fishing license required for those 16+) Stissing Pond (Pine Plains) Twin Lakes (Salisbury) Salisbury Town Grove (Salisbury) Bring snacks, maybe a book, and settle in for a peaceful afternoon. Photo: Rudd Pond Midweek and Weekend Reset Ideas Wednesday Pizza Night at The White Hart (Salisbury): Think casual vibes, cornhole on the lawn, and wood-fired pizza that hits the spot. Friday Night Picnics at Millbrook Vineyards & Winery : Pack a basket, spread out on the lawn, and let the kids run around while you soak in a gorgeous sunset and a glass of wine. Photo: Millbrook Vineyards & Winery Pack the Fun Keep a bag in the car with a few go-to items so you're always ready for a spontaneous adventure: Reusable water bottles A frisbee or small soccer ball Sunscreen and bug spray A deck of cards Picnic blanket Snacks (always) Let the rhythms of school life settle in—but don’t let them dull your sense of play. Autumn is full of small, magical moments, especially in this corner of the world. Keep your summer spirit alive by making space for spontaneity and joy, one outing at a time.

Photo of Oakhurst Diner, Captured by Olivia Valentine Millerton, NY, offers the perfect blend of small-town charm and outdoor beauty. Here is a sampling of things to do in 12 hours on a summer Saturday in our picturesque town. 10:00 AM – Morning Tea and Scones at Harney & Sons Start your day at Harney & Sons Teabar . Grab a freshly brewed tea and a delicious scone to-go. Harney & Sons is renowned for its wide variety of teas, so take your time to choose the perfect blend to kickstart your morning. Photo of the Harlem Valley Rail Trail 10:30 AM – Stroll the Rail Trail Next, head to the Harlem Valley Rail Trail with your breakfast treats. Spend an hour enjoying a leisurely walk along this scenic trail that offers a serene escape and a chance to appreciate the beautiful landscapes of upstate New York. 11:30 AM – Furniture Finds at North Elm Home Furnishings On your way back towards the village, take a short detour to visit North Elm Home Furnishings . This shop is a must-visit for anyone interested in beautiful furniture and unique pieces to add charm and character to their home. 12:00 PM – Lunch at Oakhurst Diner Before your shopping spree, stop for a hearty lunch at Oakhurst Diner . This beloved local spot offers a menu full of classic American diner fare with a modern twist. Whether you are craving a juicy burger or a fresh salad, Oakhurst Diner has something to satisfy your midday hunger. 1:00 PM – Shopping on Main Street After lunch, do some shopping on Main Street. Millerton boasts a variety of unique shops that cater to all tastes: Abode : Beautiful home goods and gifts. BES : Stylish and unique artisan products. Country Gardners Florist : Lovely floral arrangements and gifts. Designer Finds : High-end consignment clothing. Oblong Books : A paradise for book lovers. The Elephant’s Tusk : Second-hand treasures. Westerlind : Outdoor and lifestyle gear. Insider Tip: While you're here, pick up a snack from Westerlind Pantry, then head across the street to one of the village's outdoor tables to enjoy a quick pick-me-up. Photo from Millerton Antiques Center 3:30 PM – Art and Antiques Spend the afternoon exploring Millerton’s artistic and antique offerings. You never know what rare and exciting items you might discover: Hunter Bee : Vintage furniture and fun finds. Mad Rose Gallery : Local artwork and photography. Millerton Antiques Center : A treasure trove of antiques. Montage : European antiques and collectibles. 5:00 PM – Dinner at Willa As the day winds down, make your way to Willa for a fantastic dinner. This local favorite serves up dishes crafted with fresh, local ingredients. Whether you’re in the mood for a hearty meal or something light, Willa’s diverse menu has something for everyone. Photo from The Moviehouse 7:00 PM – Grab a Drink and Catch a Movie at The Moviehouse End your day with a relaxing movie at The Moviehouse . Start by grabbing a drink at their cozy bar, then settle for an intimate film-viewing experience. This charming theater provides the perfect setting to unwind after a full day of exploring and shopping. A Perfect Day in the Village From morning tea at Harney & Sons to a nightcap movie at The Moviehouse, Millerton offers a relaxing blend of activities and experiences. Whether you’re a local looking for a day out or a visitor exploring the area, our charming town provides a perfect backdrop for a memorable summer Saturday. It’s a day you won’t forget!