Top Things to Do in Massachusetts in September 2025: Festivals, Food, and Fall Fun

September is one of the best months to be in Massachusetts. The weather cools, the leaves start to turn, and the calendar is packed with festivals. From cultural celebrations and food fests to live music and family fun, there’s something happening almost every weekend.

Baystate Tent is proud to support these events with our tents, helping communities gather rain or shine — and we’d love to see you out there!

Key September Events in Massachusetts

• Our Lady of Fatima FESTA – Aug. 28–Sept. 1, Ludlow MA → Learn more
• GreekFest Somerville – Sept. 5–7, Somerville MA → Learn more
• Friendship Home’s River Rock Music Festival – Sept. 6, Hingham MA → Learn more
• Team Haverhill’s River Ruckus – Sept. 13, Haverhill MA → Learn more
• Oak & Iron Brewing Co. OAKTOBERFEST – Sept. 13, Andover MA → Learn more
• Andover Greek Food Festival – Sept. 13–14, Andover MA → Learn more
• Boston Local Food Festival – Sept. 14, Boston MA → Learn more

Our Lady of Fatima FESTA — August 28–September 1, 2025

📍 Ludlow, MA
🎟 Free admission Sunday & Monday | $3 admission Thursday–Saturday
🔗 Learn more here

Labor Day weekend in Ludlow means one thing: FESTA!

This is one of the biggest community celebrations in Massachusetts, blending faith, food, music, and culture into five days of nonstop energy. Thousands come for live concerts, authentic Portuguese cuisine, raffles, fireworks, and the moving candlelight procession honoring Our Lady of Fatima.

Baystate Tent will be everywhere at FESTA — our tents help create the spaces where families eat, dance, and celebrate. Whether you’re stopping in for dinner, catching the ABBA tribute band, or taking part in the outdoor Mass, you’ll experience FESTA under our tents.

If you’ve never been, this is the year. FESTA isn’t just a festival — it’s a tradition that makes summer in Massachusetts unforgettable.

GreekFest Somerville — September 5–7, 2025

📍 Dormition of the Virgin Mary, Somerville, MA
🎟 Free admission
🔗 Learn more here

If you’ve ever wished you could spend your September on a Greek island, Somerville has the next best thing. Every year, the Dormition Church community hosts its beloved Greek Festival, welcoming more than 10,000 visitors over one weekend.

The atmosphere is electric — with live traditional Greek music, folk dancing, and the warm hospitality that makes this festival one of the most anticipated events of the season. Of course, the star of the weekend is the homemade food: gyros hot off the grill, tender souvlaki, flaky spanakopita, and pastries like baklava and loukoumades that melt in your mouth.

But the festival is more than great food and music. It’s also the Dormition Church’s main annual fundraiser, with proceeds supporting their mission as a beacon of hope and service in the Somerville community and beyond. Whether you come for dinner, dancing, or just to soak in the culture, this festival brings the spirit of Greece to Massachusetts.

And yes — Baystate Tent will be there! Look for our big tent while you’re enjoying a gyro or baklava.

Friendship Home’s River Rock Music Festival — September 6, 2025

📍 Weir River Farm, Hingham, MA
🎟 $35 Online | $40 At the Gate
🔗 Learn More

Set at the scenic Weir River Farm, River Rock Music Festival is one of the South Shore’s most anticipated September events. This all-day celebration features seven live bands, local food favorites, and plenty of family fun.

Enjoy Rockin’ Burgers, Miss Emily’s comfort food, The Nuttiest Cookie, plus craft drinks from Pour Garden and The Decanted Wine Truck. Bring a blanket, grab a spot near the stage, and settle in for a day of music and community.

Even better? All proceeds support Friendship Home, a nonprofit enriching the lives of individuals with developmental disabilities and their families.

Baystate Tent is proud to provide a tent that sets the stage — literally — for this unforgettable event!

Team Haverhill’s River Ruckus (92.5 The River) — September 13, 2025

📍 Riverfront Park & Washington St, Haverhill, MA
🎟 Free admission
🔗 Learn more here

One of the Merrimack Valley’s favorite end-of-summer traditions, Team Haverhill’s River Ruckus brings thousands together for a full day of music, food, family fun, and fireworks over the Merrimack River.

The day begins with the Classic Car Show (12–3 PM), where antiques, muscle cars, and hot rods line Washington Street — with live commentary and trophies for fan favorites. Families can head to the Kids Zone, organized by the Haverhill YMCA, for face painting, balloon artists, touch tanks, tie-dye, and more.

As evening falls, live music takes the stage and the festival ends with a spectacular fireworks display that lights up the river. Local food vendors and community groups round out the day, making this a true showcase of Haverhill’s culture and community spirit.

Baystate Tent is proud to provide the tents that keep River Ruckus running smoothly.

Oak & Iron Brewing Co. OAKTOBERFEST — September 13, 2025

📍 Oak & Iron Brewing Co., Andover, MA
🎟 $32 (21+ includes two beers + meal), Kids under 21 free
🔗 Learn more here

Raise a glass and welcome fall at OAKTOBERFEST 2025! Hosted by Oak & Iron Brewing, this family-friendly festival is packed with Bavarian traditions, local flavor, and plenty of fun for all ages (and even pets — service dogs welcome inside the brewery).

Enjoy live music all day: The Lustige Streifenhörnchens Bavarian Band sets the mood from 1–6 PM, followed by a contemporary headliner from 7–9 PM. Festivities include the Blessing of the Beer, kids’ pumpkin painting and games, Oktoberfest trivia, a Bavarian costume contest, and the always-epic U.S. Steinholding Competition.

Your ticket ($32, 21+) includes two Oak & Iron brews and a hearty German-inspired meal (brats, burgers, or hot dogs with all the fixings). Kids under 21 enter free with an adult.

With authentic food, seasonal lagers, and classic Oktoberfest spirit, this event has become a fall staple in the Merrimack Valley. We’ll see you there!

Andover Greek Food Festival — September 13–14, 2025

📍 St. Constantine & Helen Church, Andover, MA
🎟 Free admission
🔗 Learn more here

OPA! The Andover Greek Food Festival is back, bringing two full days of authentic food, music, and family fun to the Merrimack Valley. From savory gyros, lamb, and souvlaki to sweet loukoumades, pastries, and Greek coffee frappes, you’ll find flavors that transport you straight to the islands. Pair it all with a visit to the Greek wine and beer garden and you’ve got the recipe for an unforgettable weekend.

Beyond the food, enjoy live music, dancing, a vibrant Kids Zone, and an Agora marketplace filled with Greek gifts and specialties. It’s an event that blends culture, tradition, and community spirit — and there’s something for everyone in the family.

Baystate Tent is proud to support this annual celebration — we’ll have tents set up so you can enjoy the festival rain or shine. Don’t miss the chance to experience the warmth, hospitality, and joy of Greek culture right here in Andover.

Boston Local Food Festival — September 14, 2025

📍 Rose Kennedy Greenway, Boston, MA
🎟 Free admission
🔗 Learn more here

The Boston Local Food Festival is one of New England’s most celebrated food events — and Baystate Tent is proud to have been part of it for 14 years and counting. This annual, outdoor, zero-waste festival showcases the very best in sustainable, local food, with a focus on healthy eating, local farming, and food equity.

Each September, the Rose Kennedy Greenway transforms into a vibrant celebration of farm-to-table flavors, farmers, local restaurants, food trucks, fishermen, and food producers. Visitors can sample fresh dishes, shop local ingredients, watch chef demos, and learn about the importance of supporting our region’s food system.

But the festival is more than just a foodie’s paradise — it’s a community movement. With live music, family-friendly activities, interactive exhibits, and conversations about sustainability, the Boston Local Food Festival connects people to the food they eat and the farmers who grow it.

For over a decade, Baystate Tent has helped bring this vision to life — tented rain or shine, creating spaces where community, culture, and sustainability come together. It’s one of our favorite events each year, and we can’t wait to see you there!

 

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Other Things to Do in September in Massachusetts

If festivals aren’t enough, September is also the perfect time to:

• Go apple picking at one of Massachusetts’ many orchards
• Hike the trails in the Berkshires or Blue Hills
• Take a day trip to Cape Cod or the North Shore before the season winds down
• Visit local farms for hayrides, cider, and pumpkin patches

See You This September

September in Massachusetts is all about coming together to celebrate food, music, and community. We’re so proud to partner with these incredible festivals year after year — creating spaces for people to gather, rain or shine. We can’t wait to see you out there!

Planning a fall event of your own? Contact Baystate Tent today — we’d love to help make it unforgettable.

Want to see more of our tents in action? Follow us on Instagram and Facebook for behind-the-scenes looks at these festivals and other events across New England.