Looking for things to do in Boston weekend? September in Boston is alive with energy — festivals, outdoor adventures, live music, and cultural celebrations. If you’re planning to spend your weekend in this historic yet vibrant city, here are the best activities to enjoy during the upcoming weekend of September 6–7, 2025.
The Boston Arts Festival returns with two days of live performances, local art exhibits, and food vendors. It’s the perfect way to spend a Saturday afternoon surrounded by creativity and waterfront views. Entry is free.
Cheer for the Red Sox at the legendary Fenway Park. Nothing says Boston weekend like a ballgame with friends, Fenway Franks, and the crowd’s energy. Tickets typically range from $40–$150 depending on seating.
Kick back with a refreshing drink while sailing through the harbor at sunset. Perfect for couples and groups of friends looking for a scenic evening adventure. Prices start around $45 per person.
Catch a free live performance of Shakespeare in the heart of Boston Common. Bring a blanket, grab some snacks, and enjoy world-class theater under the stars. Admission is free, but donations are welcome.
Celebrate the season at the Boston Public Market with local vendors, fresh produce, cider tastings, and live music. A great family-friendly stop for foodies and anyone looking for local flavors.
Boston’s most playful urban park hosts an outdoor movie night with lawn games, glowing swings, and plenty of food trucks. Admission is free, and it’s one of the best things to do in Boston city on a September evening.
Start your Sunday with live jazz and a delicious brunch while cruising along the Charles River. Tickets cost around $65 per person, including the buffet.
Laugh the night away at the annual Boston Comedy Festival, featuring local talents and international comedians. A must for anyone looking for weekend entertainment. Ticket prices vary between $30–$75.
Rent a kayak or paddleboard and explore Boston from the water. It’s one of the most active things to do in Boston Massachusetts in September while enjoying early fall colors. Rentals start at $20 per hour.
This open-air market is a Boston favorite, featuring food trucks, local artisans, and live music. Great for strolling and discovering unique finds. Entry is free.
Step back in history with a guided or self-guided tour of Boston’s Freedom Trail. It’s one of the best things to do in Boston if you want to mix culture with light outdoor adventure. Tours cost about $20–$35.
Take in breathtaking views of Boston Harbor and the skyline with cocktails in hand. Perfect for a stylish Saturday evening. Average drinks range $15–$25.
If you love seafood, don’t miss this festival with fresh lobster, oysters, and chowder, plus cooking demos and live music. Admission starts at $25.
Unwind with a community yoga session along the Charles River Esplanade. A healthy and energizing way to spend a Sunday morning. Most classes are donation-based.
End your weekend with live music at the iconic House of Blues near Fenway Park. Ticket prices depend on the artist, usually $40–$120.
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