Seisiún, an Irish music and cultural festival, will take place at The Stage at Suffolk Downs on September 6–7! Co-founded by Joe Killian and Liam Lynch with The Bowery Presents, the two-day event features Boston’s Dropkick Murphys and The Pogues, marking the band’s first U.S. performance in nearly 20 years and a tribute to the late Shane MacGowan. Meaning “session” in Irish, Seisiún blends iconic groups with rising talent, drawing on the legacy of the 1990s Fleadh Festival, which brought major Irish artists to Suffolk Downs. This new festival continues that tradition, showcasing music, culture, and community through a mix of both iconic and new voices.



Find more information on Greater Boston.

Soak up September on Cape Cod, also known as our Second Summer! Enjoy farmers' markets, New England's best golf, walking trails, beautiful beaches and seaside autumn festivals. At the Harwich Cranberry & Music Fest on September 13-14, shop for paintings, jewelry, photography and other works of art from local artisans, while enjoying live on-stage entertainment. The Tennesse Williams Theater Festival takes place September 25-28 in Provincetown, where legendary playwright Tennessee Williams often came for creative inspiration. And experience the best in craft beer at Cape Cod Brew Fest on September 20 at Cape Cod Fairgrounds in Falmouth. Sample from 60+ breweries and over 50 styles of beer. Find more reasons to love September on Cape Cod here!

Find more information on Cape Cod.

Nothing says ‘Fall is coming’ like The Big E! New England’s six-state fair is coming to West Springfield from September 12-28 with all of the rides, games, fair food and entertainment you’d expect from one of the top fairs in North America. You’ll want to stay in Western Mass long enough to visit The Big E but save time to add a visit to Oktoberfest at Six Flags New England, the Naismith Basketball Hall of Fame, Springfield Museums, Yankee Candle Village and MGM Springfield, too!

Find more information on Western Mass.

Photo: Lynne Graves

Explore the Hampshire County Museum Trail this September! 15+ museums and historic sites offer experiences for art aficionados, literature lovers, family outings, and more – all in a region rich with great dining, shopping, and nightlife! Outdoor fun abounds at the Amherst Block Party and the Downtown Northampton Block Party, or aboard the Lady Bea riverboat. Experience world-class music when Wynton Marsalis comes to the UMass Fine Arts Center, and when New York Voices take a bow during the multi-day Northampton Jazz Festival!



Find more information on Hampshire County.

Join us at the Johnny Appleseed Visitors’ Center for a weekend celebration of North Central Massachusetts culture and community! Happening on weekends in August, September, and October, this free, family-friendly event offers fun for all ages. Enjoy live music, henna tattoos, alpacas, crafts, face painting, cider donuts, coffee, and more. Experience the charm and spirit of the region.  Find details here!  Funded in part by local Cultural Councils and Mass Cultural Council.



Find more information on North Central Mass.

Martha’s Vineyard is September’s sweet spot! Beautiful weather highlights island beauty. Much to see/do: 20th MV International Film Festival (9/2-7); Morning Glory Farm’s Corn-Shuck & Shimmy (9/5); Featherstone’s Potters Bowl (9/7); MV Striped Bass+Bluefish Derby (9/14-10-18); HospiceMV Golf Tournament (9/14); Tivoli Day (9/20); Vineyard Charity Golf Classic (9/29). Vineyard beaches, hiking/cycling-trails, museums, exceptional shopping, world-class restaurants, fabulous lodging, sights/attractions (Mytoi/CapePoge; five lighthouses; Menemsha, 312 dazzling Gingerbread Cottages, fantastic sailing/kayaking/SUP-ing, farm stands make MV the ultimate September getaway!

Find more information on Martha's Vineyard.

From September 19– 21, experience FreshGrass at MASS MoCA! Set against the foothills of the beautiful Berkshire mountains, FreshGrass is a family-friendly festival with the best in bluegrass and roots music filling the fields, courtyards, and galleries of MASS MoCA — the largest contemporary art museum in the country (gallery admission included with all tickets!). Along with world premieres, emerging artist competitions, farm-fresh food, local brews, and pop-up jam sessions, this is three days of festival magic produced in partnership by MASS MoCA, the FreshGrass Foundation, and No Depression.



Find more information on the Mohawk Trail Region.

MetroWest festivals abound in September, offering a calendar of events that showcase local culture. Stop by the Hopkinton Polyarts 50th Anniversary Show 9/6, ASHHOP Porch Fest 9/13, Marlborough Food Truck & Arts Festival 9/14, AppleFest 2025 9/19,  Sudbury Colonial Faire and Fife 9/27 and Dragonfly Street Faire 9/27. Music lovers will be thrilled to see Kendo at the Franklin Farmers Market, Soul Function Boston at HCA 9/20 and American Idol Alum David Cook at TCAN on 9/27.



Find more information on MetroWest.

September’s palette paints Nantucket in soft evocative hues. Outside, hiking trails (9,011 acres representing 1/3 of Nantucket) and cycling trails, kayak waterways, 80 miles of beaches, ponds beckon while indoors, museums, boutiques, shops appeal to visitors. Nantucket Cottage Hospital Sankaty Swing (9/8); Cross-Island Hike (9/27); Restaurant Week (Sept/Oct); Nantucket Island Fair (9/13-14) Kayak Tours (9/4 & 9/9); Stargazing Loines Observatory (September 5/10/12/17/19/24/26); Guided-Tours Coskata-Coatue-Wildlife-Refuge, Conservation hiking trails! Kayak, SUP, sail, cruise, surf, fish! Enjoy island merchants, dining venues, stay awhile at inns-B&Bs-hotels.

Find more information on Nantucket Island.

Begin your Essex County adventure with Trails & Sails September 13–28,. Be guided through unique landscapes on land and sea, explore historic properties, and take in cultural experiences of all kinds. Don’t miss Haverhill’s River Ruckus on September 13, featuring live music, classic cars, Kids Zone, great local goods and spectacular fireworks over the Merrimack River. North Shore Music Theatre present the four-time Tony Award-winning show, RENT, September 16–28.

Find more information on North of Boston.

King Richard’s Faire is back! Come escape your reality on Saturdays, Sundays & Monday holidays from August 30–October 19. For event details, visit kingrichardsfaire.net. On September 6, the Endless Summer Waterfront Festival in Hull features food, crafts, art, entertainment and more. At the Fall Harvest Fair at Soule Homestead Organic Farm in Middleborough on September 27, meet animals, see a cranberry bog exhibit, and enjoy hay rides, live music, kids’ activities and a horse show. For all Plymouth County events, visit SeePlymouth.com!

Find more information on Plymouth County.

Southeastern MA

Enjoy Cisco Brewers New Bedford Country Fest September 5-7. In Fall River on September 6, take a step back in time for a dining experience featuring Victorian-era table etiquette and a history lesson in true crime. The  Easton300 Block Party is September 6, celebrating the town's 300th-anniversary celebration at the Governor Ames Estate. On September 7, catch the Outlaw Music Festival at the Xfinity Center. Rehoboth Agricultural Fair is September 13 at Grear Farm. First Taste of Fall at BPZOO (New Bedford) is September 13, featuring local breweries. Thai Food & Cultural Fair (Taunton) is on Sunday, September 21. South Coast Harvest Festival (Westport) is September 26 -28 at the Westport Fairgrounds. Visit our Pumpkin patches and corn mazes at Simcock Farm (Swansea), Four Town Farm (Seekonk) and Buzzards Bay Brewing (Westport).

Find more information on Southeastern Mass.

Each year, 1Berkshire collaborates with the city of North Adams to host a festive, inclusive, and vibrant downtown parade celebrating all things autumnal in the Berkshires. Join us for the 69th annual Fall Foliage Parade: To Northern Berkshires & Beyond on Sunday, October 5 at 1 pm! This year, the parade promises to be a spellbinding journey into the extraordinary, where dreams take flight and imagination knows no bounds. Floats, bands, marching units, and so much more!

Find more information on The Berkshires.

The Lowell Kinetic Sculpture Race returns on Saturday, September 20, bringing art, engineering, and imagination to the streets and waterways of Lowell! Watch as human-powered, all-terrain sculptures—part machine, part artwork—parade through downtown before tackling a rigorous course of road, mud, and the Merrimack River. This uniquely Lowell tradition blends creativity, community, and a touch of quirkiness, delighting spectators of all ages. Don’t miss one of the city’s most inventive and entertaining annual events!

Find more information on Greater Merrimack Valley.

It’s a month of Pride in Worcester, with the “Queer Met Gala of Massachusetts” (9/5) at Mechanics Hall, and a festival downtown (9/6). EcoTarium cuts the ribbon on a new exhibit, Wallace & Gromit™: Get Cracking! Silver Scream Con (9/12-14) brings a weekend of horror to DCU Center, with Nine Inch Nails performing (9/13). Maple Hill Disc Golf hosts the 8th annual MVP Open (9/25-28), with a special kick-off event held at Polar Park (9/24).



Find more information on Central Massachusetts.

Celebrate “A Blue Ribbon Affair” at the 176th Franklin County Fair, September 4–7 in Greenfield. Kick off with Thursday’s parade (5 pm), then don’t miss Friday’s MASS Truck Pull (5:30pm), Saturday’s Kids Power Wheels Demo Derby (1 pm), Stoney Roberts’ Demolition Derby both Sat & Sun (6 pm), and Sunday’s Emergency Services Parade (11 am) with family fire-safety games. All weekend long: midway rides, agricultural exhibits, Pirate Man Dan, Axe Women Loggers of Maine, FLIPPENOUT trampoline shows, Mike Piazza’s Flying High Frisbee Dogs, Team East BMX, and more. Get the full schedule and tickets here: https://fcas.com/tickets

Find more information on Franklin County.