Boston comes alive with energy every year through a packed schedule of festivals celebrating music, culture, history, food, and more. If you’re planning group travel in 2025, festivals offer the perfect reason to visit, and GOGO Charters makes it easy to get your group there with a charter bus rental in Boston.

Whether you’re coordinating airport pickups from Logan International Airport, hotel shuttles from Back Bay, or a suburban transfer from Newton or Waltham, we’ll get your group there comfortably and on time.

Skip the parking hassles and transit delays by booking private group transportation to the city’s biggest events. Call (617) 206-3898 to reserve your Boston charter bus for events today.

Rent a Charter Bus for Top Boston Festival

St. Anthony’s Feast – August 2025

The North End’s most famous summer event, St. Anthony’s Feast, fills the streets with Italian food, live entertainment, and parades. As one of the largest Italian-American festivals in the country, it’s a must-see for cultural organizations and foodie groups alike.

Navigating the North End’s narrow streets and limited parking can be tricky. Booking a bus rental in Boston means your group can enjoy the festivities without worrying about logistics.

Boston Seafood Festival – September 2025

Every September, the Boston Seafood Festival takes over the historic Boston Fish Pier in the Seaport District, celebrating the city’s maritime heritage with a clamorous mix of fresh seafood, chef demonstrations, live music, and family-friendly entertainment  Hosted by the Boston Fisheries Foundation, this annual food festival draws over 7,000 attendees giving back to a 501(c)(3) mission promoting sustainable seafood and local industry.

Attendees sample everything from lobster rolls and clam chowder to inventive new dishes showcased by more than 20 food vendors. For groups/vendors/excursion planners, utilizing a Boston charter bus rental to transport your guests ensures smooth logistics and maximum time enjoying the festival.

Boston Film Festival – September 2025

For those who love the silver screen, the Boston Film Festival is a premier cultural event. Hosted at venues like the Paramount Theatre and the Seaport’s AMC Loews, the festival showcases independent and international films, panel discussions, and red carpet moments.

Film clubs, universities, and media programs often attend in groups. If you’re planning a visit from areas like Waltham or Medford, a Boston bus rental offers a convenient and comfortable ride.

Head of the Charles Regatta – October 2025

Each fall, the Charles River becomes the backdrop for one of the world’s largest rowing competitions: the Head of the Charles Regatta. It’s a weekend packed with racing, riverside picnics, and college rivalries.

Whether you’re coordinating a team’s travel or organizing a fan group, GOGO Charters offers reliable sports team bus rentals in Boston with plenty of room for gear and spectators.

Boston Book Festival – October 25, 2025

Mark your calendars for October 2025, when Copley Square transforms into a literary hub for the Boston Book Festival. This free, all-day event celebrates the written word with author talks, panel discussions, writing workshops, and storytelling sessions for all ages. Whether you’re a lifelong bookworm, an aspiring writer, or a teacher bringing students to connect with contemporary authors, this festival is a must-attend.

Presented in partnership with local cultural organizations, the Boston Book Festival is a powerful reminder of how words can stimulate, unite, inspire, and delight. Traveling with a book club, school group, or community organization? A charter bus rental in Boston offers a simple and organized way to arrive together, avoid parking, and enjoy the day from start to finish.

HONK! Festival – October 2025

This grassroots celebration of activist street bands takes over the neighborhoods of Somerville and Cambridge each fall. The HONK! Festival is bold, musical, and full of positive energy—perfect for youth organizations, marching bands, or nonprofit groups looking for an uplifting day out.

Groups coming from Boston proper or neighboring areas can benefit from a Boston charter bus rental that includes custom pickup and drop-off points for maximum convenience.

Boston Winter Holiday Market – November–December 2025

End the year on a high note at the Boston Winter Holiday Market at City Hall Plaza. Featuring cozy food chalets, artisan gifts, and a festive ice skating rink, this European-style holiday market is a favorite for families, schools, and church groups.

Make your outing even more special by reserving a holiday bus rental in Boston with climate control, onboard entertainment, and professional drivers who know the city well.

Planning a Group Trip to Boston Festivals

Whether you’re coordinating a local field trip, planning travel from Newton or Malden, or hosting out-of-town guests, GOGO Charters offers flexible options for every group. Choose from minibuses for small outings or full-size charter buses for large crowds. You’ll get access to amenities like reclining seats, luggage storage, WiFi, and PA systems.

Before your trip, be sure to review the Boston charter bus parking guide for tips on navigating loading zones and approved drop-off areas. And if you’re coming from nearby communities,  we can also pair you with Newton bus rentals, Malden bus rentals, or bus rentals from Arlington to help bring you to your destination safely and on time.

Charter Bus Rentals for Boston Festival

Plan Ahead for Boston’s Signature Annual Events

Even though some of Boston’s biggest events—like the Boston Marathon, Boston Calling, and Boston Harborfest—have already taken place this year, they remain key highlights of the city’s cultural calendar and are worth planning ahead for in 2026.

These major festivals bring in thousands of attendees annually, creating high demand for group transportation and event logistics. If your team, school, or organization plans to attend next year, now is the perfect time to start thinking about booking a Boston charter bus rental to lock in the best availability and pricing. GOGO Charters can help you secure reliable transportation for next year’s marathon day gatherings, Memorial Day music weekends, or Fourth of July history tours.

Reserve Your Boston Festival Bus Today

From world-famous regattas to food festivals on the waterfront, Boston offers something for every group in 2025. With easy pickup options from hotels, airports, and suburbs—and transparent charter bus pricing plans to help you stay on budget—GOGO Charters is your trusted partner for Boston group travel.

Call (617) 206-3898 today to get a quote and reserve your ride to Boston’s top events.