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Holiday Events and Attractions in Cambridge and Boston

It's that time of the year! All of us have waited for the winter holidays more than anything else this year. There is something about this time of year that brings cheer to everyone! While you may not be able to experience most of the things that you enjoy every year during winter and Christmas, there are many outdoor activities and events that you can check out in Cambridge and Boston. Here are some of the activities that you can try this year! They are safe, they are outdoors, and they are fun!

Go Christmas Tree Shopping

If you have not picked your Christmas tree yet, check out Suffolk Downs' seasonal spot to purchase your tree, lights, wreaths, and holiday garlands. A former dog racing track, Suffolk Downs is outdoor, safe, and even has home delivery. 

Hop on the Classic Harbor Line Cruise

Take a break from your day-to-day life and escape to the water. Get onboard the 1920s style motor yacht and enjoy themed cruises that feature jazz music, brunch, and gorgeous winter sunsets. This year, all Classic Harbor Line Cruises are operating at 50 percent capacity. They also have designated seating zones, and all guests are required to wear masks.

Family Fun at the Mendon Christmas Drive-in

The Mendon Drive-In will be airing a holiday classic every weekend for the rest of December. Create happy family memories at this drive-in paired with a carol singalong laser light show.

Snow Shoeing and Cross-Country Skiing

Experience the outdoor adventure with snow-shoeing and cross-country skiing in Boston. You can take some fabulous courses in Concord or outside the De Cordova Sculpture Park in Lincoln, MA, where you can snow-shoe around the outdoor sculptures as well. You can also go cross-country skiing on the Weston Ski Trail.

Attend the Holiday Creator Market

Check out the Holiday Creator Market that is held at the Boston Public Market through December 17. Indulge in sustainable grocery shopping and choose from a range of sustainable gifting options. This annual artisan market is held for four weekends till Christmas. Visitors can choose from works of different artisans ranging from jewelry, home accessories, food items, and more.

Ocean Therapy Winter Walks

The Ocean Therapy Winter Walks are held by the Boston Harbor. Considering how most of us have spent the entire year indoors, this Ocean Therapy Winter Walk gives you a great chance to breathe in some fresh winter air. Take this guided therapy tour at Belle Isle Marsh and feel refreshed in the city's unique wilderness. All participants are required to wear masks and always maintain 6 feet distance from others.

The Freedom Trail

The Freedom Trail is one of the best places to visit in Boston during winters. Walk by 16 of the city's most iconic spots and the Faneuil Hall. This 2.5 miles long winding path has everything from shopping to eating to dance shows and concerts. 

Enjoy Festive Lights at the Zoo

Our local zoo is an ideal place to enjoy Christmas lights this year. Plenty of outdoor space and adorable animals will give you all the cheer you need. Visit the zoo and marvel at the LED lights that add color to all animal enclosures. 

Quincy Square Winter Market

Check out wares by local artisans and explore specialty shops at this year's Quincy Square Winter Market. This year's market will be held outdoors at Kilroy Square between the Fours and the new Hancock Parking Garage in Quincy Center. 

Trellis of Lights 2020

Visit the iconic Trellis of Lights this year at the Christopher Columbus Park. This year marks the 18th year of lighting of the park's signature trellis. Come watch the park, located on Boston's historic waterfront, be transformed into a winter wonderland. The 260 feet of trellis will be illuminated with more than 50,000 blue lights with 14 decorated trees.

No matter what event you attend or activity you do, return after a fun day to your warm and cozy rooms in our boutique hotel. With a sophisticated style and eclectic designs, our rooms at Freepoint Hotel Cambridge are perfect for you to relax after an exciting day out.


Book 3 nights, get 1 free! Extend your stay, soak in the sights, and make memories in Boston/Cambridge.

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