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Your Guide to the Best Fairs & Festivals Near Millerton This Season
- millertonbusinessa
- Jul 7
- 3 min read
Make the most of your summer and fall weekends—rides, food, music, and more!
If you're visiting Millerton—or lucky enough to live nearby—you’re in one of the best corners of the Northeast to soak up small-town charm and big-time fair fun. To help you plan, we’ve rounded up our favorite local fairs and festivals happening this season.
1. Dutchess County Fair
Rhinebeck, NY – 40 minutes from Millerton
August 19 – 24, 2025
One of the largest county fairs in New York, the Dutchess County Fair is a full-on celebration of agriculture, family fun, and local pride. Expect carnival rides, 4H animals, live music (big names, too!), craft vendors, food trucks, and more.
Local Tip: Go on a weekday if you can—the crowds are lighter and lines are shorter.
2. Columbia County Fair
Chatham, NY – 45 minutes from Millerton
August 27 – September 1, 2025
Classic in the best way. This fair offers everything from tractor pulls and demolition derbies to local crafts and blue-ribbon pies. There’s a midway full of rides, nightly music, and tons of traditional fair food.
Local Tip: Parking fills up fast. Bring cash and arrive early to beat the traffic.
3. Millbrook Firemen’s Carnival
Millbrook, NY – 25 minutes from Millerton
July 9 - 12, 2025
A beloved community event featuring rides, food booths, and one of the largest parades in Dutchess County. It’s small-town summer at its finest—and perfect for families looking for a low-key but festive night out.
4. Summer Nights of Canaan Carnival
Canaan, CT – 15 minutes from Millerton
July 16 - 19, 2025
This multi-day celebration includes everything from fireworks and rides to games and sweets. It’s a nostalgic, family-friendly event packed with small-town fun.
Local Tip: Fireworks and parade are on Saturday, July 19th.
5. Hudson Valley Hot Air Balloon Festival
Union Vale, NY – 45 minutes from Millerton
August 29 – 31, 2025
Wake up for sunrise launches or stay for the sunset glows—this festival is breathtaking. In addition to hot air balloon rides, you’ll find food trucks, live music, a beer and wine tent, and tethered balloon experiences.
Local Tip: Balloon rides sell out fast. Book online in advance if you want to go up.
6. Hudson Valley Wine & Food Fest
Rhinebeck, NY – 40 minutes from Millerton
September 6 – 7, 2025
Perfect for a grown-up weekend escape, this fest features tastings from local wineries, distilleries, and craft beverage producers—plus gourmet food trucks, artisanal vendors, and live entertainment.
Local Tip: Tickets are cheaper in advance. Designated driver passes available.
7. Goshen Fair
Goshen, CT – 55 minutes from Millerton
August 30 – September 1, 2025
An old-school fair with strong rural roots—livestock competitions, tractor pulls, fried everything, and live bands every day. It’s one of Connecticut’s best and a great way to spend Labor Day Weekend.
Local Tip: Don’t skip the barns—kids love the piglets, sheep, and dairy cows.
8. Litchfield Hills Highland Games
Lakeville, CT – 15 minutes from Millerton
September 28, 2025
Celebrate Scottish heritage with live pipe and drum performances, Highland dance, caber tossing, and more. There’s also traditional fare (hello, meat pies) and a strong sense of community spirit.
Local Tip: Bring a picnic blanket and spend the day. It’s a feast for all senses.
Helpful Planning Links:
Wrap-Up
From fireman’s parades to Scottish games to skies full of hot air balloons, there’s something for everyone just a short drive from Millerton. Whether you're here for the weekend or lucky enough to stay longer, these local fairs and festivals are worth making part of your summer and fall tradition.
Tag us in your adventures using #VisitMillertonNY—we’d love to see where you end up!
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