The 10 Can’t-Miss New England Fairs After Labor Day

As summer gives way to fall and the leaves begin their spectacular color show, New England’s fair season hits its peak. There’s something magical about a crisp September or October day at the fair — the smell of apple cider donuts, the excitement of the midway, and the pride of local farmers displaying their best produce. These fairs after August 25th capture the essence of harvest season and create memories that last a lifetime.

The Top 10 New England Fairs

1. The Big E (Eastern States Exposition) – West Springfield, Massachusetts

Dates: September 12-28, 2025
Website: www.thebige.com

Known as “New England’s Great State Fair,” The Big E is the undisputed king of New England fairs. This 17-day extravaganza is the fifth-largest fair in the nation, drawing over 1.5 million visitors who come to celebrate everything that makes our region special.

What makes The Big E truly unique is the Avenue of States, where each New England state has its own building showcasing local foods, crafts, and culture. You can travel through all six states in an afternoon — grabbing Maine baked potatoes, Vermont maple candy, Rhode Island coffee milk, New Hampshire apple cider, Massachusetts cranberry anything, and Connecticut’s famous steamed cheeseburgers.

The Better Living Center spans multiple buildings with vendors, demonstrations, and the latest innovations. Don’t miss the Big E Circus Spectacular (free with admission), the daily parade at 5 PM, or the concerts featuring national acts. Pro tip: Weekdays are significantly less crowded, and don’t forget to try the Big E Cream Puff — they sell over 50,000 of them!

2. Woodstock Fair – South Woodstock, Connecticut

Dates: August 29 – September 1, 2025 (Labor Day Weekend)
Website: www.woodstockfair.com

Celebrating over 160 years of tradition, Woodstock Fair kicks off the post-summer fair season with one of Connecticut’s most authentic agricultural celebrations. Set on historic fairgrounds that transport you back in time, this four-day event perfectly balances old-fashioned charm with modern entertainment.

What sets Woodstock apart is its dedication to agriculture education. The birthing center lets visitors witness calves, piglets, and lambs being born. The extensive 4-H and FFA exhibits showcase the hard work of young farmers. The milking parlor demonstrations happen three times daily, and you can try your hand at milking a cow yourself.

The entertainment is non-stop with three stages, including traditional folk music, contemporary bands, and children’s shows. The demolition derby on Sunday night is legendary, and the truck pulls draw competitors from across New England. Don’t miss the apple pie contest or the famous Woodstock Fair hamburgers.

3. Hebron Harvest Fair – Hebron, Connecticut

Dates: September 4-7, 2025
Website: www.hebronharvestfair.org

This charming fair marks the traditional end of summer and beginning of harvest season in Connecticut. While smaller than some others on this list, Hebron Harvest Fair maintains an intimate, community atmosphere that makes everyone feel like a local.

The fair’s gardens and flower shows are exceptional, featuring competitive exhibits that rival those of botanical gardens. The produce competitions are serious business here — the giant pumpkin weigh-off regularly sees entries over 1,000 pounds. The Heritage Animal Breeds exhibit showcases rare and historic livestock breeds that were common in colonial New England.

Kids love the barnyard scrambles, and the pig races happen four times daily. The craft barn features over 50 local artisans demonstrating traditional skills. Evening entertainment includes local bands, and the Saturday night fireworks display is choreographed to music.

4. Tunbridge World’s Fair – Tunbridge, Vermont

Dates: September 11-14, 2025
Website: www.tunbridgefair.org

Don’t let the name fool you — while it may call itself the “World’s Fair,” Tunbridge is quintessentially Vermont. This fair has been running since 1867 and maintains its authentic agricultural roots while embracing its quirky Vermont character.

What makes Tunbridge special is its setting in a natural amphitheater surrounded by Vermont’s green hills. The antique tractor parade is a highlight, featuring machines dating back to the early 1900s. The contra dancing on Friday and Saturday nights brings together locals and visitors for traditional New England dancing.

The fair is famous for its “Unique Vermont” competitions, including the husband calling contest and the nightgown parade. The midway is modest but perfect for families, and the agricultural exhibits are comprehensive. Don’t leave without trying the famous Tunbridge Fair French fries or the maple milkshakes.

5. Common Ground Country Fair – Unity, Maine

Dates: September 19-21, 2025
Website: www.mofga.org

Organized by the Maine Organic Farmers and Gardeners Association, this fair is unlike any other in New England. It’s a celebration of sustainable living, organic farming, and traditional skills that attracts over 60,000 visitors who share these values.

No carnival rides or fried dough here — instead, you’ll find over 700 vendors selling organic produce, handmade crafts, and sustainable products. The demonstration areas are incredible, with everything from timber framing to blacksmithing, spinning to solar panel installation. The renewable energy exhibits showcase the latest in sustainable technology.

The food is all organic and locally sourced, with options for every dietary preference. Live music takes place on multiple stages, featuring a diverse range of genres, including folk, bluegrass, and world music. The children’s area includes hands-on activities like apple pressing and wool carding. This is more than a fair — it’s a movement celebrating sustainable rural life.

6. Cumberland Fair – Cumberland, Maine

Dates: September 21-27, 2025
Website: www.cumberlandfair.com

Cumberland County Fair brings together the best of southern Maine for a whole week of agricultural celebration. The fairgrounds are easily accessible from Portland, making it popular with both urban and rural visitors.

The horse and oxen pulling competitions here are among the best in New England, with teams coming from across the Northeast and the Maritime provinces. The 4-H livestock shows are extensive, and the vegetable hall displays are museum-quality. The fair’s commitment to agriculture education shows in its working farm display and antique farm equipment exhibits.

The midway is one of the largest in Maine, with over 30 rides and games. The grandstand features harness racing most afternoons and concerts in the evenings. Food options range from traditional fair fare to Maine specialties like whoopee pies and fresh seafood.

7. Durham Fair – Durham, Connecticut

Dates: September 25-28, 2025
Website: www.durhamfair.com

Connecticut’s largest agricultural fair draws over 200,000 visitors to the Durham fairgrounds, yet maintains its friendly, small-town atmosphere. The hilltop location offers breathtaking views of the Connecticut River Valley, particularly spectacular during the fall foliage season.

Durham’s fruits, flowers, and vegetables competition is the largest in New England, with exhibits that would make any gardener envious. The handicraft and needlework displays include quilts that are genuine works of art. The fair’s educational focus includes extensive agricultural demonstrations and workshops throughout the weekend.

Three entertainment stages ensure non-stop action, from magic shows to tribute bands. The truck and tractor pulls on Friday and Saturday nights pack the grandstands. The demolition derby on Sunday is the season finale for many competitors. Food highlights include the Lions Club’s famous hamburgers and the Rotary Club’s baked potatoes.

8. Fryeburg Fair – Fryeburg, Maine

Dates: September 28 – October 5, 2025
Website: www.fryeburgfair.org

Maine’s Blue Ribbon Classic has been running since 1851, making it one of the oldest agricultural fairs in the country. Set against the stunning backdrop of the White Mountains, this eight-day fair is the perfect celebration of fall in Maine.

The draft horse and oxen show at Fryeburg is legendary — this is where the serious competitors come to prove themselves. The Woodsmen’s Day on Monday features competitions in ax-throwing, cross-cut sawing, and log rolling. The livestock shows are comprehensive, featuring a diverse range of animals, from dairy cattle to alpacas.

The museum farm showcases life in rural Maine from the 1800s, with working demonstrations daily. The midway features over 40 rides, and the grandstand hosts harness racing every afternoon. Evening entertainment includes nationally known country and rock acts. The fair’s apple crisp, made with local apples, is legendary.

9. Deerfield Fair – Deerfield, New Hampshire

Dates: October 2-5, 2025
Website: www.deerfieldfair.com

For over 145 years, the Deerfield Fair has been New Hampshire’s premier fall celebration, perfectly timed for peak foliage season. This family-friendly fair offers four days of traditional agricultural exhibits alongside modern entertainment.

The craft barn at Deerfield is exceptional, featuring over 100 artisans who demonstrate and sell traditional New England crafts. Watch blacksmiths forge horseshoes, potters at their wheels, and weavers creating beautiful textiles. The agricultural exhibits include everything from giant pumpkins to miniature horses.

The pig races are hilarious and happen several times daily — even adults can’t help but cheer. The demolition derby on Saturday night is one of the best in New Hampshire. The Friday night fireworks display against the October sky is magical. Don’t miss the fresh apple cider donuts or the maple cotton candy.

10. Topsfield Fair – Topsfield, Massachusetts

Dates: October 3-13, 2025
Website: www.topsfieldfair.org

America’s oldest county fair (established in 1818) provides the perfect finale to New England’s fair season. Running for 11 days during peak fall foliage, Topsfield combines centuries of tradition with modern attractions.

The Giant Pumpkin Weigh-Off at Topsfield is nationally renowned, often setting New England records with pumpkins weighing over 2,000 pounds. The bee and honey exhibit is one of the most comprehensive in the country, with observation hives where you can watch bees at work. The flower show in the Grange building features spectacular displays that rival any garden show.

The arena events include everything from sheep dog demonstrations to freestyle motocross. The demolition derbies and concerts draw huge crowds. The fair’s food offerings are extensive, but don’t miss the famous Topsfield Fair apple cider and homemade donuts — people wait in line for an hour for these treats, and they’re worth every minute.

Making the Most of Fall Fair Season

Planning Your Fair Adventures:

• Check weather forecasts and dress in layers — fall weather can be unpredictable
• Bring cash — many vendors and games don’t accept cards
• Arrive early for the best parking and smaller crowds
• Download fair maps from websites beforehand
• Consider booking nearby hotels early for weekend visits

Safety Tips for Fair Fun:

• Keep hand sanitizer handy and use it frequently
• Stay hydrated — fall sun can still be strong
• Wear comfortable, closed-toe shoes for walking on uneven ground
• Establish a meeting spot in case anyone gets separated
• Take breaks in shaded areas to avoid exhaustion

Budget-Friendly Strategies:

• Look for advance ticket discounts online (most fairs offer them)
• Pack water bottles and snacks for young children
• Set spending limits for games and stick to them
• Share large food items — portions are usually generous
• Take advantage of free entertainment and demonstrations

Making Memories:

• Enter something in the competitions — vegetables, crafts, photos
• Let kids participate in the barnyard scrambles or other contests
• Take pictures with the giant pumpkins and prize-winning animals
• Try something new — whether it’s milking a cow or eating fried pickles
• Chat with the farmers and craftspeople — their stories are fascinating

These fairs represent the heart and soul of New England as summer transitions to fall. Each offers its own unique character while maintaining those timeless elements that make agricultural fairs special. Whether you’re admiring prize-winning vegetables, cheering at the pig races, or sharing a funnel cake while watching the sunset over the midway, these fairs create the memories that define New England autumns.

The beauty of these September and October fairs is that they coincide with the fall foliage season, making the drive to and from the fairgrounds part of the adventure. Pack the car, grab the family, and experience the magic of New England’s agricultural heritage at these can’t-miss fairs. After all, there’s no better way to celebrate the harvest season than surrounded by your community, enjoying the fruits of local labor, and making memories that will warm you through the winter ahead.