Massachusetts Fall Festivals 2025: 15 Must-See Events

Ready to experience fall magic? Massachusetts hosts incredible autumn festivals that’ll make your Instagram followers jealous. When Leaves turn an orange-yellow hue, and the weather gets cooler, it prepares people to welcome the snowy winter. From West Springfield’s massive Big E celebration to Salem’s spooky-season food truck gatherings, these events showcase everything locals love about New England fall traditions.

Several events and festivals have started to unravel this time to showcase local culture, traditions, and craftsmanship. Think hayrides through vibrant foliage, artisanal craft vendors, live music performances, and seasonal treats like fresh apple cider. Discover why Massachusetts remains America’s premier destination for authentic fall festival experiences.

Each event offers something unique. Besides hiking, exploring mazes, and observing fall foliage, these events are essential for getting people into a seasonal festive mood.

Experience the charm of fall festivals in Massachusetts and New England. Enjoy apple picking, hayrides, pumpkin carving, corn mazes, and antiquing.

15 Top Fall Festivals in Massachusetts

1. The Big E – West Springfield, MA

The Big E is an annual fair in West Springfield. Eastern States Exposition is the home to the Big E. For over a century, it has offered the people livestock, innovative commercial, and diversified entertainment. This event is held for 17 days on the second Friday after Labour Day. Under the laws of the Commonwealth of Massachusetts, the organization is organized as a not-for-profit educational institution.

It showcases the awesomeness of the fall through exhibits, agriculture, and entertainment. Joshua L. Brooks proposed this idea for the events in 1917 to introduce new farming methods and establish competitive awards to benefit the farmers.

The Avenue of States and Sorrowtown Village Museum are the most remarkable features of this event. Band concerts, circuses, celebrity chefs, and famous talents are other spectrums of this event.

The State Days at the event are worth visiting if you want to honor and take pride in your state. The court of honour stage is adorned by talented artists performing from day to night. Enjoy the parade daily at 6 p.m. At the E stage, you can discover up-and-coming artists.

For the first time in Big E, a bike night will be hosted to celebrate the motorcyclists. Riders can show off their skills. The fan favourite Trailer Trash will hit the stage. This event will take place on September 25, from 4 p.m. to 8 p.m. The event also celebrates St.Patrick’s Day with full enthusiasm.

The Big E features a variety of activities, including agricultural displays, horse shows, consumer events, trade shows, and entertainment. During this, more than 25 breeds of goats, cattle, and hogs are on display. The Magic Midway features a giant wheel, various rides, a petting zoo, camel and elephant rides, and many more. A few restaurant facilities also offer food from different nations and regions.

Date: September 12 to 28, 2025. From 8 a.m. to 11 p.m.
Special Activities: State Days, Giant Slide, Bike Night
Entry Fees: Vale Pass – Adult $71.50, Children ( 6 -12) $36.50. Advance Discount Tickets (available from September 10): 1-day prices for Adults, $17.50, Children (6 -12) $11.50. Gate prices for adults $20 Children $12. Children under the age of 5 are free. Sunday to Thursday $11 after 5 p.m. Senior Citizen discounts are $16 available on Sunday – Thursday.

The Big E Parking

On-site parking is available at Gate 9. Cars/trucks are $10, Motorcycles $5.Bicycles are free. There are 1200 accessible parking spots located at Gate 9. It is on a first-come, first-served basis.

Rules For The Big E

Weapons are disallowed.
Dogs are forbidden on the fairground. Only service animals are allowed.
Professional photography and drones are banned in the premises.
Costumes are prohibited.

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2. Douglas Oktoberfest – Douglas, MA

Douglas Oktoberfest is a prominent fall festival in Massachusetts. It is a hub for non-profit organisations to raise funds. This event is getting bigger every year and is considered the best in the Blackstone Valley region. Started in the mid-1980s as a yard sale, the event now hosts 4 phases of live performances.

The event is diversified with high-calibre entertainment. Over 10,000 people gather every year. About 90 vendors line the streets with a variety of games, crafts, food, and unique items. The audience was captivated by dance routines, live bands, singers, choral groups, and shows.

It also features many games and rides for the neighbouring and local children on the church lawn. Among them, trains, moonwalks, slides, and obstacle courses are famous. Wiener dog races, antique cars, and delicious food items are the key features of this event.

Date: October 4, 2025. ( Saturday). From 9 a.m. to 4 p.m.
Special Activities: Petting Zoo, Beer Garden
Contact Info: [email protected]
Nearby Attractions: Southwick’s Zoo, Purgatory Chasm State Reservation
Address: 29 Depot Street, Douglas, MA 01516

Douglas Oktoberfest Parking

Free parking is available at the following locations: a) Soldier’s Field — 1 Mechanic Street, Douglas, MA, b) Douglas Primary School — 17 Gleason Ct, Douglas, MA, C) Municipal Building — 29 Depot St, Douglas, MA. Accessible parking is available at The Goodness Store — 328 Main St, Douglas, MA.

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3. Harpoon Octoberfest – Boston, MA

Harpoon Octoberfest is one of the celebrated fall fests in Boston. This year, the event is stepping into its 33rd year. It is the largest festival ever celebrated in the neighborhood. The event is held at Harpoon Brewery. Only people who are 21 years old or older can attend Octoberfest.

They have multiple entrances and a tented area with ample seating arrangements. It’s a haven for all bear lovers. Live oompah music, beer, food, and other forms of entertainment are the key features of this event. Pretzel eating, chicken dancing, and beer-drinking competitions are attractions here.

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Date: October 3 ( Friday) 2025 and October 4 ( Saturday) 2025.
Special Activities: Flowing Taps, Stein Hoisting Competition
Contact: 617-456-2322, [email protected]
Entry Fees: Friday – Entry with 1 beer ticket – $33.03. 3 beer ticket – $49.04. Saturday – Admission with 1 beer ticket – $43.70. 1 Beer Ticket and Lederhosen Lounge Access $70.39. Entry with 3 beer tickets $59.71, and 3 Beer Tickets and Lederhosen Lounge Access $86.40.
Nearby Attractions: Boston Tea Party Ships & Museum, The Greenway Carousel
Address: 306 Northern Ave, Boston, MA 02210

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4. Berkshire Botanical Gardens Harvest Festival – Stockbridge, MA

The Harvest Festival at the Berkshire Botanical Garden is a quintessential event. The 24-acre garden is turned into a magnificent hub for this occasion. This autumn harvest has been the center of attraction since 1934.

The salient feature of this festival is family entertainment. A tag sale with gently used and repurposed household items, jewelry, and clothes is another part of this place. The elaborate plant sale and farmer’s market are also popular here. A botanical bakery offers baked goods, chili, bisque, treats, and many more. Over 50 artisanal food and craft vendors are in the garden during this event.

Barrington Brewery offers a beer garden to make this event more fun. For children, the festival offers a variety of entertainment, including pony rides, hayrides, hay jumps, pumpkin tossing, and face painting.

The festival includes interactive music, the popular persona “The Pocket Lady,” fire dancing, a ‘Misty Blues’ concert, obstacle courses, and other entertainment. Apple squeezing is also available. Carpooling is allowed, and dogs are forbidden on the fairground.

Although the tag sale will not take place this year, visitors can still enjoy the accessories sale, featuring belts, jewelry, clothing, and scarves. Dogs are disallowed on the fairgrounds.

Berkshire Botanical Gardens Harvest Festival

Date: October 11 and 12, 2025. From 10 a.m. to 5 p.m.
Special Activities: Interactive Music with Robie Bones, Great Barrington Rudolf Steiner School Puppet Wagon Show
Contact Info: 413-298-3926, [email protected]
Nearby Attractions: Norman Rockwell Museum, Chesterwood
Address: 5 W Stockbridge Rd, Stockbridge, MA 01262

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5. Wellfleet OysterFest – Wellfleet, MA

Wellfleet Oysterfest is a traditional event in Wellfleet, Cape Cod. The event will be held the weekend following Columbus Day. It’s all about the famous shellfish, like clams and oysters, from the locals. This event is a collaboration of fishermen, shellfishermen, businessmen, and many amazing volunteers.

Local cuisine, arts, and crafts are the main attractions for both visitors and locals. Culinary programs, educational lectures, road races, and eco-tours keep visitors hooked. This two-day festival represents the local traditions. Tickets are mandatory for this event.

The main feature of this place is Oyster Shuck Off, an annual oyster shucking competition. There are raw bars, indie food vendors, and numerous food tent vendors. Many children’s activities include spelling bees and other fun games. For entertainment, there are multiple live performances on the festival grounds. A jumbo screen is available to show the main stage.

The event was first started in 2001 by Wellfleet Oyster Alliance. This oyster shuck-off competition is the biggest in America people from all over the country visit for this competition.

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Date: October 18 to 19, 2025.
Special Activities: Oyster Shuck Off, Sugarcane Duquesne Redux
Contact Info: 508-349-2510, [email protected]
Entry Fees: General admission $35. Children 12 and under are free. Wellfleet residents can use the code Fleetian25 for free entry on Sunday. Only valid address holders are eligible to use this.
Nearby Attractions: Wellfleet Historical Society & Museum, Cape Cod National Seashore
Address: 1410 Route 6, Wellfleet, MA 02667

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6. What the Fluff? – Somerville, MA

What the Fluff, a madcap festival, honors the invention of the marshmallow. Union Square Main Streets and Somerville Arts Council present this event that pays tribute to Union Square Innovation. Honours the invention of marshmallow fluff. The event was first organized in September 2005.

The theme is Fluff Union: The Sweetest Square in Somerville, which offers the sweetest taste, sounds, sight, and innovation. Several food vendors are present to make this day more memorable. Art and craft vendors will also be there. They also have a selection of merchandise, including shirts, koozies, and tote bags.

There are several live performances available for entertainment. Several antiques are hosted by Archibald Query impersonators, including marshmallow tosses and jousting. The midway games area has bowling, ring toss, and other varieties of games. Their innovation alley features youth inventors and bots that make s’mores, face painting, an open mic, and more. Parkour brings more excitement, and they have bike valets.

Date: Saturday, September 20, 2025. From 2 p.m. to 6 p.m.
Special Activities: Mayor Joe Flufftastic Innovation for Impact Award Presentation, Fluff Musical Chairs
Contact Info: 617-955-0080, [email protected]
Nearby Attractions: LEGO Discovery Center Boston, Peabody Museum of Archaeology and Ethnology
Address: Somerville Ave btwn School St and Warren Ave, Somerville, MA 02143

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7. King Richard’s Faire – Carver, MA

King Richard’s Faire is the longest-running festival in the fall of the six states in New England. This Renaissance Festival of New England provides entertainment for all ages. The 80-acre wooded space brings this festival’s fun, challenges, and excitement.

They have eight vibrant stages for live entertainment. Several talented artists and performers travel a great distance to showcase their talents. Acrobats, fire eaters, aerialists, minstrels, and others entertain the patrons. The larger-than-life puppets are another attraction here.

The knights of the king daily perform jousting on horseback. In the mud, several bawdy beggars compete. Signature cocktails, wines, roasted turkey legs, fries, chowders, and other delectable food are present at the fair.

Beautiful jewelry, unique treasures, handcrafted wares, leather fabrics, armor, and many beautiful crafts are brought for sale. Face and body painting are done here. This festival includes tarot reading, henna art, psychic readings, perfumes, scented oils, and more.

The fair offers free onsite parking. Service animals are allowed inside the fairgrounds.

King Richards Faire in Carver — King Richard’s Faire in Carver

Date: August 30 to October 19, 2025, weekends and Monday holidays. From 10.30 a.m. to 6 p.m.
Special Activities: Viking Tug O’ War on the Joust Field, Magical HP House Meetups
Contact Info: [email protected]
Entry fees: General Admission (12+), 46; Child Admission (4-11), $26. Special event prices differ from the general admission fees.
Nearby Attractions: Edaville Family Theme Park, Thomas Land USA
Address: 5 Pine Street, Carver, MA 02330.

King Richard’s Faire Parking

Parking is free. Accessible parking lots are located closer to the gate.

Rules for King Richard’s Faire

Videography exceeding the length of 3 minutes is forbidden.
Weapons are disallowed.
Outside food and beverages are banned.
Dogs are prohibited. Only certified service animals are allowed.
King Richard’s Faire is a smoke-free event.
Drone photography is forbidden.
A visitor should be 21= years old to buy alcoholic beverages.

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8. Freshgrass Festival, North Adams, MA

Freshgrass is a family-friendly festival dedicated to roots music in the Berkshire Hills’ foothills. The FreshGrass Foundation, Mass MoCA, and No Depression partnered to produce this three-day music festival. For every ticket sold, FreahGrass plants a tree with One Tree Planted.

The largest contemporary galleries of Mass MoCa, courtyards, and fields are filled with visitors. Farm fresh food, locally brewed beers, and world premieres are all about this event. Several art competitions are held to celebrate new talents. Shuttle buses are available to transport you from the campsite to the festival. They have planted 16689 trees to date.

Pop-up jamming sessions and original live programs are the keys to the festivals. Four stages are available for traditional and innovative musicians on the 16-acre campus. A Silent film, FreshScores, also played at this festival.

Special activities for kids are available at FreshKids. MASS MoCA’s kidspace is open daily and free to use.

Date: September 19 to September 21, 2025.
Special Activities: Dropkick Murphys (Acoustic), Lukas Nelson + POTR
Contact Info: 413-662-2111, [email protected]
Entry Fees: Friday, $101; Saturday, $121; Sunday, $101. 3-Day Fresh Pass: $514, 3-Day General Admission: $213, Students: $153, and Children (7+): $83.
Nearby Attractions: Western Gateway Heritage State Park, Berkshire Art Museum
Address: 1040 Mass MoCA Way, North Adams, MA 01247

Freshgrass Festival Parking

Free parking is organized by MASS MoCA and FreshGrass. There is a shuttle bus running throughout the day for remote parking. Accessible parking is available on the museum grounds.

Rules For Freshgrass Festival

Outside food and beverages are disallowed.
Weapons are forbidden.
Only service animals are allowed.
Authorized professional cameras and recording devices are allowed.
Large bags, umbrellas, and backpacks are discouraged.

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9. North Quabbin Garlic and Arts Festival – Orange, MA

North Quabbin Garlic and Arts Festival is a beloved gathering amid fall foliage. This festival has consistently impressed its neighbors and visitors. In 1999, it was first held at Solidarity Farm, and from the following year till now, it has been held at historic Foster’s Farm. This event is a celebration of the regional beauty and agricultural economy.

Over 100 exhibitors come together to showcase local produce, intricate healing arts, food, and many more. This ‘festival that stinks’ unites thousands of people across New England and hopes for a better future. There is an abundance of knowledge on sustainability, renewable energy, and local living.

North Quabbin Garlic and Arts Festival in Orange

Tons of entertainment await at the festival. Artists and performers provide endless entertainment in the three stages of the fairground. A free kids’ tent offers unlimited arts and games. The cooking demonstration, featuring numerous chefs showing garlic recipe demos, is essential to this event.

This year, the theme includes foraging for mushrooms, pollinators, flower-visiting insects, training land stewards, the Inflation Reduction Act, and forestry practices, among others. A big wood-fired Masonry Oven is another attraction of this place.

Date: September 27 and 28, 2025. From 10 a.m. to 5 p.m.
Special Activities: Hooping with Alotta Hoopla, Parent, and Baby Space
Contact Info: Check thir website
Nearby Attractions: Orange Historical Society, Millers River Environmental Center
Entry Fees: Adults $10. Students/ Seniors, EBT, WIC, and Health Connector cardholders – $5. Kids 12 and younger are free.
Address: 60 Chestnut Hill Rd, Orange, MA 01364

North Quabbin Garlic and Arts Festival Parking

On-site parking is available for carpools. Single vehicles should use the shuttle lots. Shuttle services are available every 5-10 minutes. All parking is free of charge.

Rules For North Quabbin Garlic and Arts Festival

Service animals are allowed.
Alcoholic beverages and smoking are disallowed.
Carrying cash is encouraged.

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10. Harvest Moon Festival – Onset Beach, MA

Harvest Moon Festival is a popular event hosted on Onset Beach. This reimagined occasion is one of the largest and draws more people every year. Several vendors, food trucks, chowder, chili, and other entertainment keep visitors occupied.

The Rusty Nuts Car Club of Wareham hosts antique car shows. Besides, live music, stuffie contests, face painting, a guitar raffle, and balloons for kids are a few of the attractions here. A firework goes off after all the events to end the day well.

Date: Saturday, September 27, 2025. From 10 a.m. to 5 p.m.
Special Activities: Carved Pumpkin Contest, CRANKIT!-Hits & deep cuts from the WCOZ & MTVli eras
Contact Info: 508-295-7072, [email protected]
Nearby Attractions: Cape Cod Canal Railroad Bridge, Heritage Museums & Gardens
Address: Lillian Gregerman Bandshell, 1 Union Ave, Onset, MA 02558

Harvest Moon Festival Parking

Free parking is available at Water Wizz, 3031 Cranberry Highway, and Hynes Field and Temple Lot on Union Avenue. Free shuttle services are also available from Water Wizz, and accessible parking lots are located on Union Avenue.

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11. Applefest at Wachusett Mountain – Princeton, MA

Applefest at Wachusett Mountain is a family entertainment hub for all ages. It features all things Apple and locally produced items from the past 40 years. Dogs and coolers are not allowed on the festival premises.

Great food, entertainment, and unlimited fun are the main motto of the festival. Over 100 exhibitors, a farmers’ market, live music, and locally brewed beer keep the visitors happy. The scenic fall foliage from the SkyRide acts as a magnificent backdrop.

A giant pumpkin weigh-off, a cider house, blueberry pie, and an apple pie eating contest are the most popular here. Besides that, slides, inflatables, statue carvers, stilt walkers, etc., gained popularity. For children, there are clown and balloon arts. Glimpses of eagles, hawks, falcons, and owls are a bonus.

Date: Saturday, October 18, and Sunday, October 19, 2025. From 10 a.m. to 5 p.m.
Special Activities: Skyride, Fun Side Shows
Contact Info: 978-464-2300
Entry Fees: Adult $12. Children (6 -12 years) $7. Adult with Skyride $26. Children with Skyride $20.
Nearby Attractions: Bicentennial Giant Chair, Dunn State Park
Address: 499 Mountain Rd, Princeton, MA 01541

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12. Salem Food Truck & Craft Beer Festival – Salem, MA

Food Truck Festivals of America is presenting the Salem Food Truck & Craft Beer Festival.. This two-day event is all about delicious food and refreshing drinks. Dogs are disallowed this year. The hot sauces at this festival will add a spicy feel.

Over 40 of the most popular food trucks are present on those days. From juicy, fall-off-the-bone ribs to lobster rolls and Indian cuisine, a variety of dishes from popular cuisines are available. More than 50 local brewers offer regional and nationally brewed local drinks. An artisanal corner is here that has some of the best crafts.

Live music, unlimited entertainment, and many games are also part of the event. Visitors should bring their blankets and lawn chairs for relaxing and soaking up the sun. Leashed dogs are allowed.

Date: Saturday, September 20, 2025, and Sunday, September 21, 2025. From 11 a.m. to 6 p.m.
Special Activities: Lawn Games
Contact Info: 781-956-3832, [email protected]
Entry Fees: Free.
Nearby Attractions: Salem Willows Park, The House of the Seven Gables
Address: Salem City Hall, 93 Washington Street, Salem, MA 01970

Salem Food Truck & Craft Beer Festival Parking

Street parking is available on a first-come, first-served basis.

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13. Ashfield Fall Festival – Ashfield, MA

Ashfield Fall Festival is celebrated in the foothills of the Berkshire Mountains. Since 1970, it has been one of the celebrated fall events in the locality. It’s a place to collect fundraisers for various service organizations.

This hilly festival is all about showcasing local businesses and arts. It creates an opportunity for youth to develop their creativity and skills. Several games and fun activities make the event more exciting. Rope ladders, marble mazes, catapults, and pirates’ toss are among the favorites.

All the food vendors offer seasonal, locally produced food dishes. Several maple offerings are available. Many handmade crafts, pottery, barns, glass blowers, jewelry, and more are available. Exhibitor of furniture, instruments, baskets, and fabrics showcase their artistry. Merchandise is available here.

The proceeds from the Fall Festival t-shirt sales, parking lots, crafts, and exhibitors will go directly to the Fall Festival Scholarship Fund. The Ashfield Citizens Scholarship & Community Fund organization provides academic scholarships to needy students. Dogs are forbidden on the festival grounds.

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Date: October 11 and 12, 2025. From 10 a.m. to 5 p.m.
Special Activities: Cloudbelly Duo, Pumpkin Games: pumpkin relay races, bowling
Contact Info: [email protected]
Entry Fees: Free.
Nearby Attractions: Three Sisters Sanctuary, Bridge of Flowers
Address: Salem City Hall, 93 Washington Street, Salem, MA 01970

Ashfield Fall Festival Parking

Parking is available in 4 public lots this year. These are the Upper Park off Main Street, the tennis court and beach lots off Buckland Road, the Field playing field off Buckland Road, and the Ashfield Community Preschool lot on Baptist Corner Rd. FRTA and the Shelburne Falls Senior Center have organized a shuttle service. Accessible parking is available on the south corner.

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14. Topsfield Fair – Topsfield, MA

Topsfield Fair is one of the oldest county fairs in Topsfield. For over 200 years, it has been people’s favorite event. Several people, both locals and visitors from other neighborhoods, visit this festival every year. Parades, a premium flower show, vegetables, and fruits are displayed here. Fine Arts, canning, crafts, and winemaking are added perks of this fair.

They have a midway full of different rides for both kids and families. Some fast-moving, stomach-turning rides are available for teenagers. It has the largest bee-keeping and honey exhibits in North America. Four live hives are kept on display at the fair. Bee-related arts and crafts are on display.

State Police and the Sheriff Department’s K-9 perform a demonstration during the fair. A parade is held on Tuesday, Wednesday, and Thursday. Only guide dogs are allowed. The Topsfield Fair Beer Garden offers visitors a selection of beers and wines. Wheelchair rental is available.

Traditional agricultural competitions, such as horse pulling, oxen pulling, sheep dog trials, touch-a-truck, and stock framer tractor pulling, are part of this event. Live performances, such as motor stunts, the New England Rodeo, Clay Walker, the Flying Wallendas, and Demolition Derby, are featured. Several savory and dessert items are available here.

Date: October 3 – October 13, 2025. From 4 p.m. to 10 p.m.
Special Activities: Mrs. Essex County Pageant, Cock Crowing Contest & Hen Flying Contest
Contact Info: 978-887-5000, [email protected]
Entry Fees: Advanced Fair Admission Ticket $15 and Advanced Fair Ride Tickets $33. Children under 8 are free.
Nearby Attractions: Mass Audubon’s Ipswich River Wildlife Sanctuary, Wenham Museum
Address: 207 Boston St, Topsfield, MA 01983

Topsfield Fair Parking

Parking is $15 at all lots. It is located on Route 1 and 97. On weekends and holidays, additional parking is available. All parking lots have accessible spots near the gates. A shuttle service is provided to take visitors from the parking lot to the fairgrounds. Parking is free on the opening day.

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15. Johnny Appleseed Arts & Culture Festival – Leominster, MA

This festival is dedicated to the birthday of John Chapman. He’s also known as Johnny Appleseed for introducing apple trees throughout the United States and Canada. He was born in Leominster, Massachusetts. The city organizes this fall festival annually to celebrate the history and indulge in different apple-filled dishes.

For Johnny Appleseed Arts & Culture Festival, every year, the downtown turns into a hub for live music, handmade crafts, fresh apple crisps and desserts, a kids’ party zone, ice cream, donation centers, and many more. The festival is open for 8 hours. There are more than 230 vendor booths, including Webster First’s Fitchburg Branch. Visitors can enjoy a fresh breakfast, lunch, and different snacks here.

Johnny Appleseed Arts & Culture Festival, MA

You will also find the Leominster Emergency Communication Center booth here. Local thrift store booths encourage people to donate here. There are two stages for live music performances on the ground. This fun-filled long fall festival is a must-visit for every local to celebrate the birthday of a hero.

Date: September 9, 2025
Special Activities: Live Music, Kids’ Parking Lot Party.
Contact Info: 978-660-2313, [email protected]
Nearby Attractions: Coggshall Park, Curious Escape Rooms.
Address: 25 West Street, Downtown Leominster, MA, United States

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Find More Fall Festivals Near You

Conclusion

These are the most beloved fall Festivals in Massachusetts. They are unique in their way, but similar in a sense to get people into autumn moods. All these events represent the regional culture. It allows businessmen, craftsmen, and artists to develop their skills. They are a representation of the vibrant nature of the fall season. Visit these events and enjoy the beautiful autumn celebrations.

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