Massachusetts is a quintessential New England destination where autumn unfolds in all its glory. As the air turns crisp and the landscape is painted in fiery reds, oranges, and yellows, the state becomes a haven for fall enthusiasts. From the rolling Berkshires to the charming towns along the coast, every corner of Massachusetts offers a unique taste of the season.
Boston’s historic parks, like the Boston Common and Public Garden, come alive with vibrant foliage, offering a picturesque backdrop for a stroll. Venture out to the nearby Arnold Arboretum, where the rich colors of fall blend seamlessly with the serene natural landscape. The scenic byways of Western Massachusetts lead you through quaint towns like Stockbridge and Lenox, where tree-lined streets and charming inns create a storybook setting.
Massachusetts fall festivals celebrate the season’s essence with events ranging from lively harvest fairs to traditional craft shows. Festivals like the Topsfield Fair, the nation’s oldest agricultural fair, and the Wellfleet OysterFest capture the season’s spirit with local flair and a festive atmosphere. Whether you’re enjoying a pumpkin festival on the North Shore or indulging in cider and donuts at an orchard in the Pioneer Valley, these celebrations highlight the best of autumn in Massachusetts.
The Big E (Eastern States Exposition)
The Big E, America’s largest multi-state fair, is a grand celebration that brings together all six New England states for an epic festival of food, music, and entertainment. Held in West Springfield, Massachusetts, the fair is conveniently located at 1305 Memorial Avenue, making it easily accessible from across the region. Spanning a vast area with multiple buildings and outdoor spaces, the fairgrounds offer ample parking and a wide array of attractions. Visitors can explore state houses showcasing the best of each New England state, as well as barns, an arena, and a lively midway filled with rides.
Running for 17 days each September, the 2024 Big E will take place from September 13 to 29, with gates open daily from 8:00 AM to 10:00 PM—though the midway often stays open later. While weekends draw the largest crowds, weekdays offer a more relaxed experience. The Big E boasts an extensive lineup of activities and attractions, from its famous Big E Cream Puff to a variety of regional delicacies available at numerous food trucks and vendors. Live music, farm animals, craft displays, and carnival rides fill the fairgrounds, with special events like parades, horse shows, and cooking demonstrations adding to the excitement. Competitions abound, with participants vying for prizes in categories such as crafts, baked goods, and livestock. For those looking to shop, hundreds of vendors offer everything from local art to kitchen gadgets, ensuring there’s something for everyone at this iconic New England event.
Wellfleet OysterFest
The Wellfleet OysterFest is a cherished fall tradition on Cape Cod, drawing thousands each year to celebrate the town’s renowned oysters, local art, and vibrant community spirit. Set in the heart of downtown Wellfleet, Massachusetts, this two-day festival offers a picturesque coastal setting for a weekend of festivities. The charming streets of this seaside town come alive as visitors stroll along Main Street, exploring quaint shops and galleries while indulging in freshly shucked oysters. The event spreads across the town center, with food stalls, art displays, and music stages creating a lively and immersive experience.
Held annually on the weekend after Columbus Day, the 2024 Wellfleet OysterFest will take place on October 19-20. This timing allows guests to enjoy the crisp fall air and the stunning autumnal beauty of Cape Cod. Over the course of two full days, attendees can savor the best oysters the town has to offer, browse local art inspired by the coastal landscape, and soak up the festive ambiance that permeates the event. Many visitors turn the festival into a weekend getaway, staying in nearby accommodations to fully immerse themselves in the celebration.
The Wellfleet OysterFest is a feast for the senses, centered around the town’s iconic oysters. Visitors can sample these delicacies straight from local farmers and witness thrilling shucking contests where experts showcase their skills. Live music from local bands adds to the energetic atmosphere, while art lovers can admire and purchase works from talented local artists. With over 20,000 attendees, the festival buzzes with activity yet retains a friendly, close-knit vibe. Beyond oysters, a variety of seafood and other culinary delights are available from local vendors, complemented by cooking demonstrations and educational talks on oyster farming for those eager to learn more about this vital industry.
Salem Haunted Happenings
Salem Haunted Happenings is a month-long extravaganza that transforms the historic city of Salem, Massachusetts into a thrilling Halloween wonderland. Throughout October, this iconic destination becomes a spooky playground, offering parades, festivals, and eerie attractions that draw visitors from around the world. Set against the backdrop of Salem’s rich history, particularly its infamous witch trials, the event blends the city’s storied past with modern-day Halloween fun, creating a unique and immersive experience.
The festivities are centered in downtown Salem, with key locations including the Salem Common, Essex Street, and Congress Street, all within easy walking distance of each other. The city’s cobblestone streets and historic landmarks provide the perfect setting for the season’s spooky celebrations. Salem Haunted Happenings kicks off with the Grand Parade, typically held in early October—in 2024, this will take place on October 2nd from 6:30 p.m. to 8:30 p.m. The parade sets the tone for a month of continuous events, with weekends and Halloween night drawing the largest crowds and most elaborate festivities.
Salem Haunted Happenings offers something for everyone, from family-friendly activities to more adult-oriented thrills. The Grand Parade is a lively spectacle of music, costumes, and community spirit, with participants of all ages. The Haunted Happenings Marketplace, open on weekends and holidays, is a popular spot for visitors to browse local crafts and fall-themed goods on Salem Common. A highlight of the celebration is the Hallowed Harvest Jack-o-Lantern event, where hundreds of intricately carved pumpkins create an enchanting, glowing display that delights guests of all ages. Since its inception in 1982, Salem Haunted Happenings has grown from a modest local event into one of the most anticipated Halloween celebrations in the country, drawing over 50,000 visitors in its first year alone and continuing to grow each season.
Cranberry Harvest Celebration
The Cranberry Harvest Celebration is a cherished autumn event in Massachusetts, celebrating the state’s vibrant cranberry industry. Held at Patriot Place in Foxborough, this festival provides visitors with a unique opportunity to witness the bright red cranberries being harvested at the Ocean Spray Cranberry Bog. The location is easily accessible, with ample parking, and the nearby Nature Trail offers a picturesque setting to enjoy the fall colors while learning about cranberry cultivation.
Scheduled for Saturday, October 19, 2024, the 14th Annual Fall Harvest Celebration is a one-day event that promises a day full of fun and education. The festivities typically take place during the day, allowing families and friends to fully immerse themselves in the activities. The cool, crisp October weather is perfect for outdoor events, enhancing the overall experience.
The Cranberry Harvest Celebration offers a variety of activities for all ages. Visitors can watch live cranberry harvesting demonstrations, giving a rare insight into the unique method of collecting the berries. The event features cranberry-themed food and drinks, local artisan crafts, and family-friendly activities like face painting and a petting zoo. Adults can enjoy sampling cranberry wines or chatting with local growers, while live music adds to the festive atmosphere. Admission is usually free, making it an affordable outing, though visitors should bring cash for food, drinks, and souvenirs. Comfortable shoes are recommended for walking around the bog area.
Franklin County CiderDays
Franklin County CiderDays is a cherished fall festival in western Massachusetts, celebrating apples, cider, and local culture with tastings, tours, and events. Spanning several picturesque towns across Franklin County, including Ashfield, Deerfield, and Shelburne Falls, the festival takes place amid scenic orchards and cideries that showcase the region’s rural charm.
Held annually in early November, CiderDays typically runs for a full weekend, coinciding with peak fall colors and apple harvest season. In 2024, the festival will celebrate its 30th anniversary, with dates likely falling on the first weekend of November.
CiderDays offers a variety of activities for cider enthusiasts and families alike. Visitors can sample both hard and sweet ciders, tour cideries, and attend workshops on cider-making and apple varieties. The event also features apple picking, cider-pairing dinners, and live music, creating a festive atmosphere that highlights Franklin County’s rich apple-growing heritage. With its blend of local flavor and natural beauty, CiderDays is a must-visit for those looking to experience the essence of fall in Massachusetts.
Topsfield Fair
The Topsfield Fair is a cherished Massachusetts tradition that blends agricultural exhibits, thrilling rides, and family-friendly entertainment, offering a perfect mix of New England’s rural heritage and modern attractions. Located in the picturesque town of Topsfield, about 30 miles north of Boston, the fairgrounds are easily accessible from Main Street, with ample on-site parking, though carpooling is recommended during peak times.
Running for 11 days in early October, the 2024 Topsfield Fair is scheduled from September 27 to October 7. This timing offers visitors the chance to enjoy the crisp fall weather and vibrant foliage that New England is known for.
The fair features something for everyone, from agricultural exhibits showcasing prize-winning livestock and produce—like the renowned giant pumpkin contest—to hands-on experiences such as petting farm animals and pony rides. The midway brims with exciting carnival rides and games, while food vendors serve up both classic fair treats and local specialties. Live entertainment, including musical performances and comedy acts, runs daily across multiple stages, and the fair culminates in a grand parade filled with colorful floats and marching bands. Educational displays and craft demonstrations further enrich the experience, celebrating the region’s agricultural history and artisanal traditions.
King Richard’s Faire
King Richard’s Faire is a beloved Renaissance festival in Carver, Massachusetts, offering a delightful mix of entertainment, food, and activities for visitors of all ages. Set in a magical forest on 80 acres of wooded land at 235 Main Street, the festival transports guests back to the Renaissance era with its immersive atmosphere and spacious, outdoor venue.
The 2024 season of King Richard’s Faire runs from August 31st to October 20th, open on weekends and Monday holidays, including September 2nd and October 14th. With gates opening at 10:30 a.m. and closing at 6:00 p.m., visitors have 7.5 hours each day to fully enjoy the experience.
King Richard’s Faire features eight stages of live entertainment, including jousting tournaments, comedic mud pit shows, and performances by costumed actors who bring the Renaissance to life. Guests can interact with knights, jesters, and royalty as they explore the grounds, shop for unique crafts from artisans, and enjoy exciting rides and games. The festival also offers hearty Renaissance-style food and a variety of beverages, enhancing the overall experience. Ticket prices vary, with adult tickets (ages 12+) starting at $39 and children’s tickets (ages 4-11) at $20 from September 2-30, with potential increases later in the season.
Harvest Happenings at Lookout Farm
Lookout Farm in South Natick, Massachusetts, offers the quintessential New England fall experience, where visitors can enjoy seasonal activities, taste farm-fresh apples, and create lasting memories in a picturesque setting. Just a short drive from Boston, the farm is nestled on beautiful land with rolling hills and scenic views, making it a perfect destination for a fall outing. The address is 89 Pleasant Street South, Natick, MA 01760, and ample parking is available.
Fall festivities at Lookout Farm typically run from early September through late October, with the 2024 harvest season starting on September 7th. The farm is open daily from 10 a.m. to 5 p.m., with extended hours on select dates for special events. Weekends, especially in mid-October, are particularly popular, so advance tickets are recommended.
Lookout Farm offers a range of activities for all ages. Visitors can pick their own apples from over 20 varieties, explore the pumpkin patch, or take a hayride through the scenic property. Kids can meet farm animals like goats, sheep, and chickens, or try their luck navigating the corn maze. On weekends, live music enhances the festive atmosphere. The farm store offers fresh cider, apple pies, and other seasonal treats, while the on-site taproom serves hard cider and beer made with farm-grown ingredients. Food trucks frequently visit, providing tasty lunch options. Comfortable shoes and weather-appropriate clothing are recommended, and bringing a picnic is encouraged to fully enjoy the grounds.
Cape Cod Brew Fest
The Cape Cod Brew Fest is a beloved annual celebration of American craft beer, drawing enthusiasts to sample a wide variety of brews in a lively, festive atmosphere. Held at the spacious Cape Cod Fairgrounds in Falmouth, Massachusetts, the event provides ample room for dozens of breweries to set up tasting stations, with plenty of space for attendees to explore. The fairgrounds are easily accessible from across Cape Cod and offer ample parking.
The twelfth annual Cape Cod Brew Fest is set for Saturday, September 21, 2024, running from 2:00 PM to 5:30 PM. This schedule allows beer lovers to spend a full afternoon enjoying the event, with time to explore other Cape Cod attractions before or after the festival.
Featuring over 50 breweries and more than 150 styles of beer, the Cape Cod Brew Fest offers an extensive selection for attendees to sample, from light lagers to bold IPAs and rich stouts. The event is strictly for those 21 and older, with tickets providing unlimited beer samples. Live music enhances the festive vibe, while food trucks and vendors offer a variety of snacks and meals to complement the brews. The festival highlights both well-known and smaller local breweries, offering a diverse and exciting range of craft beers for guests to discover.
Deerfield Oktoberfest
Deerfield Oktoberfest brings the lively spirit of Bavarian culture to the picturesque village of Historic Deerfield, Massachusetts. This event offers a delightful blend of German-inspired festivities, including traditional food, music, and beer, all set against the charming backdrop of colonial-era buildings and scenic farmland. As visitors stroll through the historic streets, they can enjoy the vibrant fall colors that add to the festive atmosphere. The main events are centered near the Deerfield Community Center, with parking available in designated lots around town and shuttle services providing easy access to the event area.
Typically held on a weekend in late September or early October, Deerfield Oktoberfest runs from noon to 10 PM on Saturday and noon to 6 PM on Sunday. The exact dates vary each year, so it’s best to check the official Deerfield town website for the most current information. Arriving early is recommended to fully enjoy the day’s activities and avoid the crowds.
Deerfield Oktoberfest features a delightful mix of German and New England traditions. Visitors can savor German-style beers, including local craft brews, and indulge in classic fare like bratwurst, pretzels, and apple strudel. Live music, featuring traditional German tunes and popular favorites, creates a lively atmosphere, with dance areas for those eager to try out polka moves. Family-friendly activities include pumpkin painting, face painting, and hay rides, while a craft fair showcases handmade goods from local artisans. Tickets are available at the entrance, with varying prices for adults, seniors, and children. It’s advisable to bring cash, as not all vendors may accept cards.
Berkshire Botanical Garden Harvest Festival
The Berkshire Botanical Garden Harvest Festival is a cherished autumn tradition in New England, celebrating the beauty of fall in the Berkshires with local crafts, food, and activities. Held at the 24-acre Berkshire Botanical Garden in Stockbridge, Massachusetts, the festival offers a picturesque setting where colorful fall foliage enhances the event’s charm. Located at the intersection of Routes 102 and 183, the garden is easily accessible, and Stockbridge’s quaint charm and rich cultural heritage make it the perfect backdrop for this iconic celebration.
Scheduled for October 12-13, 2024, the Berkshire Botanical Garden Harvest Festival runs from 10 a.m. to 5 p.m. each day, providing visitors ample time to explore. This beloved tradition, now nearing its 90th year since its inception in 1934, coincides with peak fall foliage season in New England, offering a stunning visual experience.
The festival transforms the garden into a lively hub of autumn activities. Visitors can explore a variety of local vendors selling handmade crafts, artisanal foods, and seasonal decorations. Highlights include a farmers’ market with fresh produce, live music, children’s activities, garden tours, and art exhibitions. Food stands offer quintessential New England flavors, from apple cider to pumpkin treats and hearty soups. Celebrating the region’s agricultural heritage, the festival showcases the best of the Berkshires’ local talent and products.
North Adams Fall Foliage Festival
The North Adams Fall Foliage Festival is a cherished autumn tradition in the Berkshires, celebrating the region’s breathtaking fall colors with a festive parade and family-friendly activities. Held in the charming city of North Adams, Massachusetts, the festival centers around downtown, where spectators gather along Route 8 to enjoy the parade against a stunning backdrop of the Berkshire Mountains’ vibrant autumn foliage.
Scheduled for Sunday, October 6, 2024, the North Adams Fall Foliage Festival marks the height of the fall season. The main parade kicks off at 1:00 PM, offering visitors the perfect opportunity to experience the peak of the region’s colorful landscape. The festivities often begin earlier in the week with a children’s parade, setting the tone for the celebration.
The highlight of the festival is the Fall Foliage Parade, a beloved tradition since 1955. This lively procession features colorful floats, marching bands, and community groups, with a new theme each year that inspires creative costumes and decorations. Throughout the festival, families can enjoy a variety of activities, including a children’s fair with games and entertainment. Local businesses and food vendors line the streets, offering regional specialties and handmade crafts. The festival not only showcases the beauty of the Berkshires but also brings together locals and tourists in a vibrant celebration of all things autumnal. Nearby hiking trails further invite visitors to immerse themselves in the stunning fall scenery, making the North Adams Fall Foliage Festival a highlight of the season.
Pick One and Go!
Take in the festive spirit of New England this autumn by attending one of these unforgettable fall festivals. Whether you’re sampling local flavors, exploring scenic landscapes, or enjoying lively parades, each event offers a unique and enriching way to celebrate the season.
