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! 

Looking for some ideas of how to make the most of the long weekend? We've got a few options to honor Boston’s past and present. 

1. Free Admission to the Museum of Fine Arts
The MFA in Boston is a great place to escape the heat (hopefully not the rain). The museum offers free admission on Memorial Day.  It’s a big museum with a lot to see, but we recommend the Art of the Americas Wing. There are portraits of Boston’s key players in the buildup to the American Revolution, some of Paul Revere’s silver, and much more! 

2. Join Ye Olde Tavern Tours for a tour along the Freedom Trail
If you want to learn more about the events in Boston that led to the Revolutionary War, join us on Ye Olde Tavern Tours on Saturday or Sunday. We’ll visit ten historic sights along the Freedom Trail, drink craft beer where they planned the Boston Tea Party, and talk about the “shot heard round the world” at Lexington and Concord. HUZZAH!

3. Boston Common’s Garden of Flags
Honor Memorial Day with the Massachusetts Military Heroes organization, which places 37,000 flags on Boston Common every year to commemorate the Massachusetts service members who have lost their lives since the Revolutionary War. It’s a powerful display. 

4. Brunch on a Monday 
Brunch is everywhere in Boston on a Saturday or Sunday, but brunch on a Monday is nearly impossible to find. Two of our favorite breakfast joints will be open and they serve beer too, if you want it to be a boozy brunch. The Friendly Toast has locations in Back Bay and Cambridge and The Paramount has locations downtown and in South Boston.

5. Check out a day game at Fenway Park
Cap off the long weekend with a Red Sox game at Fenway Park on Monday afternoon. Several Red Sox players cut the 1943 season short to join the war effort, including Ted Williams and Johnny Pesky (the namesake of Pesky Pole)!