1. Holiday Pop-Up Bar
We love festive holiday drinks at Ye Olde Tavern Tours! If you do too, we might see you at a Miracle pop-up bar around Massachusetts. This popular event started in NYC and now spreads holiday cheer worldwide, including the Marlowe Hotel in Cambridge, Mystic Station in Malden, and the Citizen in Worcester. Given Boston’s history as a major rum producer, we recommend the “Bad Santa,” a rum-based cocktail with citrus, spices, and coconut! Open the day after Thanksgiving through Christmas.
2. Boston Common Tree Lighting
Boston is not short on holiday cheer when it comes to lighting up the city. If you want to see one of the biggest tree lighting ceremonies in action, head to the Visitor’s Information Center on Boston Common on Thursday, December 5th from 6-9pm. There will be refreshments, music, and (of course) Santa until the lights start coming on around 7:55pm. Over 80 trees throughout the Common and Public Garden will be lit up.
Also, while you’re in the area check out the historic neighborhood of Beacon Hill. Quaint Charles Street will close down to cars from 6-9pm. You can get a start on your holiday shopping and enjoy the carolers!
3. Ice Skating on Frog Pond
The Boston Common gets festive during the day time too – check out the frog pond for some ice skating! Open at 10am every day over the winter (except some holidays), adults skate for $6 and children (under 58 inches) get in free. You can also rent skates and skating aids.
4. Boston Beers + History
Start the holiday season off right with Ye Olde Tavern Tours! We’ll take you down the Freedom Trail, serve up some New England winter beers, and teach you about Boston’s history, including an epic snowball fight that ended in the…you’ll have to join us to find out!
5. Santa Speedo Run
If a Turkey Trot sounds like a bit much for you (a whole 5K?!), we have the perfect holiday training regimen--the Santa Speedo Run! On Saturday, December 14, join a group of runners/drinkers on a one-mile run through Back Bay, which starts and ends with libations. One minor detail: Most of the runners will only be wearing speedos and Santa hats! While the costume isn’t necessary, they do recommend dressing in holiday cheer and helping out the Play Ball! Charity, which you can do as a spectator as well.
6. SoWa Holiday Weekend
We love the South End's SoWa market (short for South of Washington St.) on any Sunday, but it’s especially festive during the holidays. It will be open in the evening on Friday, December 6 and all day December 7 and 8 for a special holiday weekend. It’s always full of art, shops, and food, but to get into the holiday spirit there will be ice sculptures, handmade gifts, and holiday DIY workshops as well!