Weekend Activities in Boston for September 2025
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.
1. Boston Arts Festival at Christopher Columbus Waterfront Park
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.
2. Red Sox Game at Fenway Park
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.
3. Boston Harbor Sunset Cruise
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.
4. Shakespeare on the Common – Free Outdoor Theater
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.
5. Boston Public Market Fall Harvest Celebration
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.
6. Outdoor Movie Night at Lawn on D
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.
7. Jazz Brunch Cruise on Charles River
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.
8. Boston Comedy Festival
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.
9. Kayaking on the Charles River
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.
10. SoWa Open Market
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.
11. Boston Freedom Trail Walk
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.
12. Rooftop Drinks at Lookout Rooftop Bar
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.
13. Boston Seafood Festival
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.
14. Outdoor Yoga at the Esplanade
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.
15. Live Concerts at House of Blues Boston
End your weekend with live music at the iconic House of Blues near Fenway Park. Ticket prices depend on the artist, usually $40–$120.
🌟 Top 3 Restaurants in Boston
- Union Oyster House – America’s oldest restaurant, perfect for seafood lovers. Official Website
- Mamma Maria – Elegant Italian dining in the North End. Official Website
- Row 34 – Trendy spot known for oysters and craft beer. Official Website
☕ Best 3 Cafes with Scenic Views
- Tatte Bakery & Café – Popular for pastries and coffee with stylish Boston vibes. Official Website
- Thinking Cup – Overlooks Boston Common, perfect for a relaxing break. Official Website
- Lookout Rooftop Café – Great coffee with skyline views. Official Website
🏨 Best 3 Hotels & Budget-Friendly Stays
- The Godfrey Hotel Boston – Central location, chic design, average rates $230/night. Official Website
- HI Boston Hostel – Affordable and social stay, rates around $55/night. Official Website
- Boston Park Plaza – Historic hotel near Boston Common, average rates $190/night. Official Website