The air is getting crisp, the leaves are starting to turn, and the scent of cider donuts is in the air—all signs that fall fair and festival season has officially arrived in Central Massachusetts! There’s no better way to celebrate the season than by gathering with family and friends at a local fair, full of music, food, and classic fall fun. We’ve rounded up a list of the very best fall fairs and festivals in and around Central Mass so you can mark your calendars and get ready to celebrate everything this beautiful season has to offer.
Thank you to our wonderful sponsor, who makes this guide possible, Precision Home Services.
Below are some of the bigger fall fairs happening:
The Spencer Fair (Spencer)
This fair runs from August 29th to September 1st. The Annual Spencer Fair is an old-time, traditional country fair featuring ox and horse pulls, cattle, rabbit, and poultry shows, hall exhibits, a midway, and outdoor entertainment, promising a great time for all who attend.
The Woodstock Fair (Woodstock, CT)
This fair runs from August 28th to September 1st. It is Connecticut’s largest agricultural fair, and also one of the oldest. The Woodstock Fair is a five-day fair held in South Woodstock, CT. “Always Labor Day Weekend” is their motto, and the fair opens at 4pm the Thursday before Labor Day and runs through Labor Day Monday, closing at 8pm. Admission is $15, Seniors & Active Military w/ ID is $10, children 10 years and under are free, and Thursday Night Admission is $10.
The Sterling Fair (Sterling)
The Sterling Fair is a two-and-a-half-day (September 5th-7th), family-oriented, community and agricultural fair. It features rides, horse pulls, oxen pulls, tractor pulls, helicopter rides, antique engine and machinery show, livestock shows, food, entertainment, and more!
West End Creamery Fall Festival & Corn Maze (Whitinsville)
Open Friday nights and weekends mid-Sept through Oct. Check the website for ticket information.
Davis Mega Maze (Sterling)
Opens this fall, check the website for details on attractions and ticket information.
The Great Jack O’lantern Journey (Southwick’s Zoo, Mendon)
Open from 5pm-close from Sept 26th to Oct 31st. Check the website for ticket information.
The Big E (Springfield)
The Topsfield Fair (Topsfield)
King Richard’s Faire (Carver)
King Richard’s Faire is the New England Renaissance Festival, filled with entertainment and fun for all ages! It runs from August 30th until October 19th.
Jack-O-Lantern Spectacular at Roger Williams Park Zoo (Providence, RI)
Jack-O-Lantern Spectacular: Trivia – 2nd Edition returns with a brand-new batch of brain busters carved into the glow of thousands of pumpkins. It’s chapter two of the ultimate fall challenge. The pumpkin trail is open nightly from 6pm-10:30pm, last entry at 10pm from September 26th to November 1st.
Below are local fall fairs and festivals by date:
August 30th & 31st, 2025
Appleseed Country Fair at Red Apple Barn (Phillipston)
Pick your own apples, sunflowers, pumpkins, and blueberries. Enjoy live music all weekend long by local bands. Vendors, face painting, food trucks, country fair activities, hayrides, dunk tank, “cow” milking, line dancing, pie baking contest, and so much more! $15 per carload, and hours are 10am-6pm.
Fall Craft and Food Festival at Hardwick Vineyard & Winery (Ware)
Kick off the fall harvest season at Hardwick Winery, shop from 70+ local artisans and crafters, indulge in some delicious Local food trucks, and kick back with a glass of Hardwick Wine! Live music, Free to attend, free to park! Fun for all ages! Hours are 11am-4pm.
September 1st, 2025
Appleseed Country Fair at Red Apple Barn (Phillipston)
Pick your own apples, sunflowers, pumpkins, and blueberries. Enjoy live music all weekend long by local bands. Vendors, face painting, food trucks, country fair activities, hayrides, dunk tank, “cow” milking, line dancing, pie baking contest, and so much more! $15 per carload, and hours are 10am-6pm.
September 6th, 2025
Fall Festival Opening Weekend at Stowe Farm (Millbury)
Opening weekend for Apple picking, country store, BBQ, saloon & live music. Train, hay, pony, and moo-choo rides. Mechanical bull, corn cannon, moonbounce. Enjoy the petting zoo, parakeet enclosure, baby animal feeding, pig races, and more. Hours are 10am-2pm.
Harvest Craft Fair at Brookfield Orchards (North Brookfield)
Browse unique handmade goods and meet the makers, and help them kick start their Fall season with fun, shopping, and fresh air! Hours are 10am-4pm.
September 7th, 2025
Harvest Craft Fair at Brookfield Orchards (North Brookfield)
Browse unique handmade goods and meet the makers, and help them kick start their Fall season with fun, shopping, and fresh air! Hours are 10am-4pm.
September 13th, 2025
Fall Festival at Eastleigh Farm (Framingham)
Ice cream, Animals, Food, Music, and local shopping $10 admission, which includes parking. Hours are 10am-4pm.
September 13th & 14th, 2025
Fall Fest at Old Sturbridge Village (Sturbridge)
Spend the day with your family and friends in the vibrant surroundings of New England’s largest outdoor living history museum. Enjoy the CowParade, a public art exhibit on display throughout the Village through the end of September! Check the website for schedules and details. Included with admission ticket. Hours are 9:30am-5pm.
Fall Artisan Festival at Lilac Hedge Farm (Rutland)
Enjoy afternoon music from 1-4pm or stay after the festival for an evening show from 5-8pm. In addition to our Farm Kitchen & Bar, we are excited to host additional food options from food truck friends to keep you well-fed all day long. For those seeking more unique animal visits, you can visit The Backyard to see our KuneKune pigs, ostrich, emus, yaks, peacocks, and more to come for the 2025 season. Enjoy a new playground or choose to enter our separate inflatables area with bounce experiences for kids from little to big! Hours are 11am-5pm.
Apple Fest at Hollis Hills Farm (Fitchburg)
There will be a variety of PYO apples, local vendors, live music, and specialty food and drinks! Hours are 11am-4pm.
September 20th, 2025
Johnny Appleseed Festival (Leominster)
Join us for food, fun, music, vendors, and more in Downtown Leominster. The festival starts at 9am. There is free parking and admission!
Leicester Harvest Fair (Leicester)
Family Fall Festival at Capen Hill Nature Sanctuary (Charlton)
This is a free event starting at 10am! Come enjoy Capen Hill’s beautiful property as it transitions to autumn, take part in some fall festivities, visit their animal residents in the Visitor Center, and jump-start your holiday shopping with local artists.
Fall Festival at A.W. Brown’s Pet and Garden (East Longmeadow)
Hours are from 10am-2pm. They will have food trucks, local vendors, activities, and so much more!
Pepperell Fall Festival (Pepperell)
This event is free to the community from 10am-3pm. They typically have over 100 local area crafters, food vendors, entertainers, and businesses participate each year.
Pumpkin Somethin’ Fall Festival (Seekonk)
They have over 50 Vendors, Entertainment, Face Paint, Sand Art, Games, Prizes, Raffle Baskets, 50/50 Raffles, Food, and so much more! Great Family Fun from 10am-3pm.
Fall Harvest Weekends at Silver Bell Farm (Monson)
They have scenic tractor-pulled wagon rides, scavenger hunt corn maze (Goat-Themed!), pumpkin patch, gourds, carving supplies & seasonal produce, gift shop, Santa’s Barnyard – meet their new goats! Two bounce houses, barrel train rides, kids’ crafts and gingerbread cookie decorating, a different local food truck every weekend, and ice cream treats & seasonal beverages. There is no admission fee to enter the farm—play areas, outdoor games, and the pumpkin patch are all accessible free of charge.
Kidfest at Wachusett Mountain (Princeton)
Saturday is Dino Day so get up close and personal with some scaly creatures. Children under 5 are free! Live animal shows, circus acts, walkaround characters, and more are all included with your tickets. Food trucks serve up everything from egg rolls to shaved ice. Hours are 11am-5pm.
September 21st, 2025
Fall Harvest Weekends at Silver Bell Farm (Monson)
They have scenic tractor-pulled wagon rides, scavenger hunt corn maze (Goat-Themed!), pumpkin patch, gourds, carving supplies & seasonal produce, gift shop, Santa’s Barnyard – meet their new goats! Two bounce houses, barrel train rides, kids’ crafts and gingerbread cookie decorating, a different local food truck every weekend, and ice cream treats & seasonal beverages. There is no admission fee to enter the farm—play areas, outdoor games, and the pumpkin patch are all accessible free of charge.
Kidfest at Wachusett Mountain (Princeton)
Sunday is Princess & Pirate Day, so come dressed in your best costume and get ready for some magic. Children under 5 are free! Live animal shows, circus acts, walkaround characters, and more are all included with your tickets. Food trucks serve up everything from egg rolls to shaved ice. Hours are 11am-5pm.
September 27th, 2025
Fall Harvest Weekends at Silver Bell Farm (Monson)
They have scenic tractor-pulled wagon rides, scavenger hunt corn maze (Goat-Themed!), pumpkin patch, gourds, carving supplies & seasonal produce, gift shop, Santa’s Barnyard – meet their new goats! Two bounce houses, barrel train rides, kids’ crafts and gingerbread cookie decorating, a different local food truck every weekend, and ice cream treats & seasonal beverages. There is no admission fee to enter the farm—play areas, outdoor games, and the pumpkin patch are all accessible free of charge.
Harvest Fest at Southwick’s Zoo (Mendon)
Explore a variety of unique, handcrafted goods from talented local artisans. Enjoy live music from talented local artists. Savor the flavors of the season in our beer garden (21+) featuring a variety of craft beers and ciders. Included in zoo admission, and hours are 10am-5pm.
Townsend’s Fall Festival (Townsend)
Crafters, vendors, paint your own pumpkins, build your own scarecrow, Children’s games, Pie by the slice/specialty cakes, entertainment, Uncle Joey’s Cannoli Truck, Las Lemonade, and Tasty Fry food trailer. Hours are 11am-4pm.
St. Bridget Community Fall Festival (Framingham)
The Festival starts at 11am, so go and enjoy our chili cook-off, play games, explore food trucks, and browse local vendors.
September 28th, 2025
Fall Harvest Weekends at Silver Bell Farm (Monson)
They have scenic tractor-pulled wagon rides, scavenger hunt corn maze (Goat-Themed!), pumpkin patch, gourds, carving supplies & seasonal produce, gift shop, Santa’s Barnyard – meet their new goats! Two bounce houses, barrel train rides, kids’ crafts and gingerbread cookie decorating, a different local food truck every weekend, and ice cream treats & seasonal beverages. There is no admission fee to enter the farm—play areas, outdoor games, and the pumpkin patch are all accessible free of charge.
Harvest Fest at Southwick Zoo (Mendon)
Explore a variety of unique, handcrafted goods from talented local artisans. Enjoy live music from talented local artists. Savor the flavors of the season in our beer garden (21+) featuring a variety of craft beers and ciders. Included in zoo admission, and hours are 10am-5pm.
W.H.A.T. Family Fall Festival (Wilbraham)
Get ready for a fun day filled with pumpkin decorating, cornhole tournaments, student-staffed snack shack, bounce houses, a climbing rock wall, obstacle courses, s’mores roasting, apple picking, Fieldcrest brews, special treats, and live entertainment. Hours are 12pm-4pm.
October 4th, 2025
Douglas Oktoberfest (Douglas)
Vendors line both sides of Main Street, offering crafts, food, games, and unique displays. Throughout the day, entertainment from singers, bands, choral groups, dance routines, and variety shows captivates audiences. Rides and games are prominently displayed on the church lawn, allowing easy access by families with small children, and there is a Huge Slide, moonwalk, train, and obstacle course. Hours are 9am-5pm.
Fall Fest at Wildwood Farm (Westminster)
Maker’s market, live music, food trucks, outdoor bar, and kids’ activities. Hours are 10am-4pm.
Pumpkin Palooza! at Tougas Family Farm (Northborough)
Celebrate the season at their Pumpkin Festival—a perfect fall day out for family and friends! Wander the patch to pick your own pumpkins, enjoy delicious autumn-inspired foods, and sip on local brews while taking in the crisp harvest air. With plenty of activities, flavors, and festive fun, it’s the ultimate way to make memories together this fall. Hours are 10am-5pm.
Fall Harvest Weekends at Silver Bell Farm (Monson)
They have scenic tractor-pulled wagon rides, scavenger hunt corn maze (Goat-Themed!), pumpkin patch, gourds, carving supplies & seasonal produce, gift shop, Santa’s Barnyard – meet their new goats! Two bounce houses, barrel train rides, kids’ crafts and gingerbread cookie decorating, a different local food truck every weekend, and ice cream treats & seasonal beverages. There is no admission fee to enter the farm—play areas, outdoor games, and the pumpkin patch are all accessible free of charge.
Fall Festival at The Overlook (Charlton)
Enjoy a day filled with vendor booths, live music, hayrides, games, prizes, and seasonal treats. This year, they are expanding with even more crafters and artists and specialty foods, cheeses, spices, wine and beer tasting, food trucks, local restaurants, and farm stand produce. Hours are 11am-4pm.
Hey Day at Wachusett Meadow Wildlife Sanctuary (Princeton)
Journey by hayride through the meadow, canoe on Wildlife Pond, and children’s activities including pumpkin painting, crafts, and games. Live music by local musicians and shop with local vendors for handmade items and crafts. Admission is $10 per person or $30 per carload, and ages 2 and under are free. Hours are 11am-4pm.
October 5th, 2025
Fall Harvest Weekends at Silver Bell Farm (Monson)
They have scenic tractor-pulled wagon rides, scavenger hunt corn maze (Goat-Themed!), pumpkin patch, gourds, carving supplies & seasonal produce, gift shop, Santa’s Barnyard – meet their new goats! Two bounce houses, barrel train rides, kids’ crafts and gingerbread cookie decorating, a different local food truck every weekend, and ice cream treats & seasonal beverages. There is no admission fee to enter the farm—play areas, outdoor games, and the pumpkin patch are all accessible free of charge.
Pumpkin Palooza! at Tougas Family Farm (Northborough)
Celebrate the season at their Pumpkin Festival—a perfect fall day out for family and friends! Wander the patch to pick your own pumpkins, enjoy delicious autumn-inspired foods, and sip on local brews while taking in the crisp harvest air. With plenty of activities, flavors, and festive fun, it’s the ultimate way to make memories together this fall. Hours are 10am-5pm.
Fall Festival (Dudley)
Enjoy a free trunk or treat! There will be food trucks, carnival games, and vendors, too! Hours are 11:30am-2:30pm.
Fall Festival at Pilgrim Day Camp (Framingham)
Live entertainment & performances, live band playing upbeat favorites for all ages, magic show that will dazzle kids and adults alike, Animal Encounters Petting Zoo with friendly farm animals, inflatable corn maze, local vendors offering unique, seasonal goodies, glitter tattoos, face paint, and so much more! Hours are 1pm-4pm.
October 11th, 2025
Apple Country Fair (Brookfield)
It will showcase the work of more than 90 local artisans and feature live music, lawn games, baked goods, food trucks, raffles, and an apple pie contest—all to benefit the Brookfield Community Club. Hours are 10am-4pm.
Fall Harvest Weekends at Silver Bell Farm (Monson)
They have scenic tractor-pulled wagon rides, scavenger hunt corn maze (Goat-Themed!), pumpkin patch, gourds, carving supplies & seasonal produce, gift shop, Santa’s Barnyard – meet their new goats! Two bounce houses, barrel train rides, kids’ crafts and gingerbread cookie decorating, a different local food truck every weekend, and ice cream treats & seasonal beverages. There is no admission fee to enter the farm—play areas, outdoor games, and the pumpkin patch are all accessible free of charge.
Fall Fest at Hollis Hills Farm (Fitchburg)
There will be PYO pumpkins, PYO apples, local vendors, live music, kids’ crafts, and specialty food and drinks! Join us for a weekend full of fun, music, delicious food, and good times. Hours are 11am-4pm.
Fall Harvest Festival (Chelmsford)
Enjoy a fantastic day shopping with vendors, food, face painting, a cash bar, and raffles. Hours are 11am-3pm.
October 12th & 13th, 2025
Fall Harvest Weekends at Silver Bell Farm (Monson)
They have scenic tractor-pulled wagon rides, scavenger hunt corn maze (Goat-Themed!), pumpkin patch, gourds, carving supplies & seasonal produce, gift shop, Santa’s Barnyard – meet their new goats! Two bounce houses, barrel train rides, kids’ crafts and gingerbread cookie decorating, a different local food truck every weekend, and ice cream treats & seasonal beverages. There is no admission fee to enter the farm—play areas, outdoor games, and the pumpkin patch are all accessible free of charge. Hours are 10am-5pm.
Fall Fest at Hollis Hills Farm (Fitchburg)
There will be PYO pumpkins, PYO apples, local vendors, live music, kids’ crafts, and specialty food and drinks! Join us for a weekend full of fun, music, delicious food, and good times. Hours are 11am-4pm.
October 18th, 2025
Oktoberfest at Tougas Family Farm (Northborough)
Food, beer, music, games and more! Free admission. Hours are 9am-5pm.
Farm Days at Waters Farm (Sutton)
They have an antique tractor/ engine show, animal exhibition, 4H animals, craft vendors, tractor pull, food vendors, barrel train, kids’ bouncy houses, robotics club, police/fireman meet and greet, hammer mill, pottery demonstration, peddler shop, tractor-pulled hay rides, apple crisp, and farm house tours. Hours are 10am-4pm.
Harvest Fest (Sturbridge)
Handmade items to purchase of all varieties, feed the goats, check out the alpacas, vote on some chowder, and more! Hours are 10am-4pm.
Fall Harvest Weekends at Silver Bell Farm (Monson)
They have scenic tractor-pulled wagon rides, scavenger hunt corn maze (Goat-Themed!), pumpkin patch, gourds, carving supplies & seasonal produce, gift shop, Santa’s Barnyard – meet their new goats! Two bounce houses, barrel train rides, kids’ crafts and gingerbread cookie decorating, a different local food truck every weekend, and ice cream treats & seasonal beverages. There is no admission fee to enter the farm—play areas, outdoor games, and the pumpkin patch are all accessible free of charge. Hours are 10am-5pm.
Applefest at Wachusett Mountain (Princeton)
Featuring every apple-flavored treat from candy to cocktails, and one of the most unique bird’s eye views of Fall foliage in Massachusetts. Enjoy hot apple cider, fresh cider donuts, apple soda & more from the Red Apple Farm stand. Hours are 11am-5pm.
October 19th, 2025
Oktoberfest at Tougas Family Farm (Northborough)
Food, beer, music, games, and more! Free admission. Hours are 9am-5pm.
Fall Festival at Apex Orchards (Shelburne)
Their Fall Festival has live music, craft vendors, food, drinks, pre-picked pumpkins, and PYO apples with tractor-drawn wagon rides. Hours are 10am-3pm.
Farm Days at Waters Farm (Sutton)
They have an antique tractor/ engine show, animal exhibition, 4H animals, craft vendors, tractor pull, food vendors, barrel train, kids’ bouncy houses, robotics club, police/fireman meet and greet, hammer mill, pottery demonstration, peddler shop, tractor-pulled hay rides, apple crisp, and farm house tours. Hours are 10am-4pm.
Harvest Fest (Sturbridge)
Handmade items to purchase of all varieties, feed the goats, check out the alpacas, vote on some chowder, and more! Hours are 10am-4pm.
Fall Harvest Weekends at Silver Bell Farm (Monson)
They have scenic tractor-pulled wagon rides, scavenger hunt corn maze (Goat-Themed!), pumpkin patch, gourds, carving supplies & seasonal produce, gift shop, Santa’s Barnyard – meet their new goats! Two bounce houses, barrel train rides, kids’ crafts and gingerbread cookie decorating, a different local food truck every weekend, and ice cream treats & seasonal beverages. There is no admission fee to enter the farm—play areas, outdoor games, and the pumpkin patch are all accessible free of charge. Hours are 10am-5pm.
Applefest at Wachusett Mountain (Princeton)
Featuring every apple-flavored treat from candy to cocktails, and one of the most unique bird’s eye views of Fall foliage in Massachusetts. Enjoy hot apple cider, fresh cider donuts, apple soda & more from the Red Apple Farm stand. Hours are 11am-5pm.
Fall Festival (Grafton)
Join in at Nelson Park in North Grafton for Scarecrow Building and Pumpkin Painting from 11AM to 2PM. There will be music, inflatables, food trucks, and local businesses joining in on the fun! This event is free.
October 24th, 2025
Pumpkin Walk at Choate Park (Medway)
Get ready for a ghoulishly good time filled with tricks, treats, and Halloween excitement for all ages from 7pm-9pm.
October 25th & 26th, 2025
Pick or Treat at Tougas Family Farm (Northborough)
There will be lots of Halloween fun with apples and candy at the Farm! This event is perfect for little ghouls and boils and their families who want the excitement of wearing their favorite costume while having a Halloween farm adventure! Admission is $15 per ticket; pre-registration is required. Hours are 10am-3pm.
Castleberry Fall Craft Festival (Wilmington)
With over 175 booths, this curated marketplace showcases a diverse selection of handcrafted treasures, including artisan pottery, cozy upcycled mittens, intricate decorative paintings, custom-built furniture, and so much more. Whether you’re looking for seasonal décor, unique gifts, or something special for yourself, you’ll find one-of-a-kind creations made by skilled artisans from across the region. Indulge in seasonal flavors! Treat yourself to gourmet delights like chocolate toffee, handcrafted peanut butter cups, buttery shortbread cookies, farm-fresh cheeses, and more—perfect for holiday entertaining or a little personal indulgence. Plenty of free parking is available. Hours are 10am-5pm. Admission is $10.00 per adult, and children under 14 are free!
Fall Harvest Weekends at Silver Bell Farm (Monson)
They have scenic tractor-pulled wagon rides, scavenger hunt corn maze (Goat-Themed!), pumpkin patch, gourds, carving supplies & seasonal produce, gift shop, Santa’s Barnyard – meet their new goats! Two bounce houses, barrel train rides, kids’ crafts and gingerbread cookie decorating, a different local food truck every weekend, and ice cream treats & seasonal beverages. There is no admission fee to enter the farm—play areas, outdoor games, and the pumpkin patch are all accessible free of charge. Hours are 10am-5pm.
Fall extends into November with these festivals:
- 11/15: Fall Food Truck Festival in Ludlow from 12pm-5pm
- 11/22-11/23: Thanksgiving Harvest Festival at Red Apple Barn in Phillipston from 10am-5pm
