5 Things to Do in Boston Around the Holidays
The jolliest time of the year is just around the corner, and we’re officially getting into the holiday spirit!
To celebrate this festive season, we put together a curated list of our five favorite things to do in Boston during the holidays. Whether you’re planning a romantic date, hanging out with friends, or exploring the city on your own, these spots are sure to bring the magical vibes.
Seaport’s annual holiday market turns the neighborhood into a magical Christmas getaway. This is a must if you’re in town this winter.
Shop the sweetest local gifts, enjoy a hot drink, and soak in the winter fun. If you’re looking for a cute outing with your girlfriends, add this to your list.
Location: 100 Seaport Blvd, Boston, MA 02210
Dates: Open seven days a week from November 7 through December 28, 2025
This indoor festival lets you enjoy all things Christmassy without freezing. It’s a true Boston favorite — and this year marks their 10th anniversary!
Wander around with a holiday-themed cocktail, try specialty bites, and explore over 125 local makers, artists, and food vendors.
Location: SoWa Power Station, 550 Harrison Ave, Boston, MA 02118
Dates: November 28 – December 28, 2025
Christmas-Decorated Bars & Restaurants
If you’re looking for the most extra holiday atmosphere (and truly giant cocktails), this is your spot. The interior is bold, colorful, and full of photo-ready corners. They also just launched their new Santa’s Wonderland menu — worth checking out for the full experience.
Stratus Winter Oasis at View Boston
For unbeatable views of the city lights, head up to Stratus. Besides having the highest views in Boston, they also serve some incredible cocktails. There’s no way you’ll leave this cocktail lounge without feeling merry!
They’re in full holiday mode and hosting festive events all season long. Think of flashy decor, cheery cocktails, and melt-in-your-mouth bites. A portion of their proceeds will be donated to The Greater Boston Food Bank to help fight food insecurity this holiday season.
Don’t miss their holiday wreath-making on Thursday, December 4, or gingerbread decorating on Thursday, December 11.
Ice Skating on Frog Pond
There’s something oh so Christmas-movie-like about heading to a park, renting skates, doing a few laps, and warming up with hot cocoa afterward. Keep an eye out for the official opening date on their site and wish for snow!
Soak in the Holiday Feels at Beacon Hill
Take a stroll around Beacon Hill to see the twinkling lights on Boston Common and the charmingly decorated brownstones. Pro tip: The cutest holiday photos are taken on Acorn Street.
If you want to skip the walking, hop onto the Festive Nights Trolley Tour for cozy views, see the city’s annual Christmas tree, and learn a bit of Boston history.
There’s a little something for everyone in the city this holiday season. We hope you enjoy it to the fullest!