How to celebrate Thanksgiving in Boston

Known as “The World’s Greatest Bake Sale,” Pie in the Sky, Community Servings’ annual bake sale, is now in its 30th year. The seasonal fundraiser allows folks to purchase pies prepared and donated by more than 150 local chefs, bakers and restaurants. The proceeds support the not-for-profit food and nutrition program, which provides services throughout Massachusetts to individuals and families living with critical and chronic illnesses. Pies—whose flavors include pumpkin, apple, pecan —go for $30 a pop and enable Community Servings to provide tens of thousands of scratch-made, diet-specific meals throughout the year. If spending the night before Thanksgiving rolling out pie dough doesn’t tickle your fancy, snag one of theirs to bring to dinner instead. 

Set sail this Thanksgiving on CityCruises’ Thanksgiving Day Afternoon Lunch Cruise, which provides stunning views of the Boston skyline and historic waterfront landmarks, all while you enjoy a celebratory lunch buffet. The two-hour cruise departs from Commonwealth Pier in the Seaport. Buy your tickets beforehand. 

If you’re feeling a bit sluggish after the big meal, a stroll in one of the Emerald Necklace parks will reinvigorate you. Accessible, free, and available throughout Boston and Brookline with over 5 miles of walking paths and 1,100 acres of green space, it’s the perfect way to get some fresh air. Catch the foliage at the Arnold Arboretum or creep around the abandoned bear cages at Franklin Park. The full map is available online here, or use the mobile app as your guide. It even has a guide for those with strollers.

From soup kitchens to shelters, there are worthy organizations in the Commonwealth that welcome your assistance on Thanksgiving. However, there are tons of groups putting in the work beforehand to ensure that all families in Massachusetts get to celebrate Turkey Day. For example, the United Way of Massachusetts Bay and Merrimack Valley provides Thanksgiving essentials to area families, which is especially needed these days, since nearly 1 in 5 households struggles to put food on the table. Before Thanksgiving comes around, find out what you can do to help them feed 20,000 families. More info here.

Don’t worry about feeding the meters. While it may not take up all your holiday, knowing that parking in Boston is free on holidays should certainly add a little spring in your step. 

An impressive Thanksgiving dinner begins with impressive hors d'oeuvres. Formaggio Kitchen has everything you need to wow your guests. Peruse cases full of artisanal cheeses from around the world, then move on to charcuterie and the perfect complementary condiments. Pick up a few sweet treats for after dinner, too. For dinner itself, you’ll find plenty of interesting grains, beans, salts, spices, and other ingredients to make a spectacular dish.

Sometimes the best thing to do on Thanksgiving is absolutely nothing. Leave the bickering with family members to others, and instead curl up on the couch to watch these iconic holiday traditions. First, the Macy’s Parade, where you can watch pop stars lip sync and float through Herald Square, and then the National Dog Show as you eat whatever you want in front of the TV.

Thanksgiving mornings in the Boston area are bustling with high school football games, which can get extremely lively and provide tremendous people watching, not to mention a hell of a tailgate party. Grab a crew of friends and a few blankets and watch the high school rivalries get fierce.

The largest Thanksgiving Day race in the city of Boston is the Franklin Park Coalition’s 9th Annual Turkey Trot 5K. Open to all ages and paces, the joyful run also welcomes strollers, wheelchairs, and race-ready leashed dogs. There will be awards for fast finishers, as well as those who sport a good costume. Sign up beforehand here.

Your favorite local spots that stay open for the holiday are always filled with folks looking to have a good time. Baramor in Newton will have special holiday hours all weekend long, and will be open late-night on Thanksgiving Eve and the holiday itself. If you’re looking to pop by for dinner, they recommend making reservations. 

You're going to have to earn those Thanksgiving calories, so why not take a hike or two? There are plenty of quality hikes near Boston that are easy to get to. Whether it’s climbing a lung-busting hill or exploring trails through scenic wooded reservations, these Boston hikes offer relaxation and a healthy dose of fresh air that will have you ready for Thanksgiving.

Walk off all the turkey and sides by strolling around the famous arboretum, open daily including on Thanksgiving. Search for the last remaining splashes of fall color as you enjoy fresh air and natural beauty. After some fresh air and a brisk stroll, you might just be ready for some leftovers.