Seasons of Discovery: Your Guide to Cambridge and Boston’s Best Events in 2025
Cambridge and Boston are cities that thrive on culture and connection, and 2025 promises a calendar full of experiences to match their spark. From the buzz of live music on summer nights to the fiery foliage in fall, every season brings new invitations for immersion. At Freepoint Hotel Cambridge, Tapestry Collection, we’re your gateway to both Cambridge and Boston, offering a restful retreat and a launchpad for exploration.
WINTER WONDERS: JANUARY–MARCH
Charles River Farmers Market
When: Open year-round, hosted indoors December–April
The Charles River Farmers Market keeps the spirit of local food alive all winter long. Stroll through the cozy red sheds and browse tables of fresh, seasonal produce, locally baked bread, and handcrafted pastas. It’s the perfect way to start a brisk winter morning in Cambridge.
A Global Stage: World Figure Skating Championships
When: March 25–30
This March, Boston takes the spotlight as the World Figure Skating Championships arrive at TD Garden. Watch the world’s best skaters execute awe-inspiring jumps and spins in an arena alive with energy. Whether you’re a lifelong fan or a first-time spectator, the artistry and athleticism are guaranteed to amaze.
SPRING AWAKENS: APRIL–JUNE
Boston Marathon
When: April 21
Few events embody Boston’s spirit like the Boston Marathon. Join thousands of spectators, feel the city’s pulse as runners power through historic streets, and cheer on athletes from around the globe. The camaraderie brings Boston together, embodying the city at its best.
Harvard Arts First Festival
When: May 1–4
Harvard’s legendary indoor and outdoor spaces burst to life with this annual showcase of music, theater, dance, film, and visual arts. Wander Harvard Yard as stages come alive with theater productions, concerts, and open dance rehearsals—an immersive celebration of Cambridge’s artistic community.
Boston Calling Music Festival
When: May 23–25
Kick off summer with one of the region’s biggest music festivals. Held at the Harvard Athletic Complex, Boston Calling fills the air with big names, animated crowds, and the thrill of discovering global headliners and local favorites.
SUMMER VIBRANCE: JULY–SEPTEMBER
Cambridge Jazz Festival
When: July 26-27
Jazz fans won’t want to miss the Cambridge Jazz Festival, where Denehy Park transforms into a lively space filled with soulful melodies and a welcoming community vibe. Grab a bite from local food vendors, unfold a blanket on the lawn, and let the smooth sounds take over.
Kendall Square Lunchtime Concerts
When: Weekly, June–August 2025
For an intimate summer experience, the Kendall Square Lunchtime Concert series offers weekly live performances by local and regional artists. It’s a mellow way to wind down after navigating Cambridge’s bustling streets.
Boston Harborfest
When: July 2–4
Celebrate Independence Day in one of the country’s most historic cities. Join this family-friendly festival and enjoy historical reenactments, art markets, Chowderfest, live musical entertainment, and the iconic crackling of fireworks over Boston Harbor.
Cambridge Science Festival
When: September 23–29
Dive into a world of discovery at MIT Museum’s Cambridge Science Festival. From interactive exhibits to engaging workshops and talks, this city-wide event is perfect for curious minds of all ages.
FALL TRADITIONS: OCTOBER–DECEMBER
Head of the Charles Regatta: A Fall Classic
When: October 17–19
Autumn in Cambridge is incomplete without the Head of the Charles Regatta. Feel the rush as rowers slice through the glassy waters of the Charles River, framed by autumn’s stunning leaves and the cheers of thousands lining the riverbanks. This historic race captures the essence of a quintessential New England experience.
Holiday Shopping in Harvard Square
When: November–December
As the holidays approach, Harvard Square glows with twinkling lights, and boutique windows beckon with unique holiday treasures. Sauntering through feels like stepping into a holiday postcard—warm, festive, and full of charm.
WHY FREEPOINT IS YOUR EVENT-DAY HAVEN
No matter which event brings you to the Northeast, Freepoint Hotel is here to make your stay exceptional. From our modern, art-inspired rooms to the inviting Secret Garden Lounge, every detail is designed with your comfort and curiosity in mind. Savor locally crafted dishes and cocktails at Freepoint Kitchen & Cocktails or join us for memorable evenings like Beer & Burger Sundays and Martini Mondays—rituals that bring locals and travelers together.
When the day winds down, let Freepoint Hotel be your sanctuary for rest, connection, and inspiration. Book your stay now, and make 2025 a year to remember.