Keep the Summer Spirit Alive: Local Adventures for Busy School-Year Routines

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.