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! 

No visit to Boston’s Museum of Fine Arts would be complete without seeing the 3,000 years of history housed in the Art of the Americas wing. Covering four floors, you can tour North, Central, and South America in just a couple of hours… but our favorite exhibits feature Revolutionary-era Boston! The museum is open seven days a week, with free admission (donations always welcome) Wednesdays after 4pm. 

1. John Singleton Copley’s famous portraits of Samuel Adams, John Hancock, Joseph Warren, and Mercy Otis Warren
Copley painted these players in Revolutionary Boston as events heated up in the late 1760s and early 1770s (to learn more, join us on a Freedom Trail tour)! Copley was born in Boston and was the town’s preeminent portrait painter, but he married a loyalist and set sail for London in 1774, never to return. Our podcast, Beer Makes History, episode #7 talks more about Copley and the men and women he painted.

2. Paul Revere’s Sons of Liberty Bowl and other metalwork
Made of silver and engraved in 1768, this bowl honors the “Glorious Ninety-Two,” members of the Massachusetts House of Representatives who refused to rescind a letter they signed protesting the Townshend Duties of 1767. You’ll find more of Revere’s work encased nearby this national treasure.

3. 18th-century Furniture
You'll have serious design envy when you see some of the gorgeously intricate furniture pieces. The MFA has several different items that were created in New England and are in amazing condition. This bookcase and desk will make you want to take out some paper and quill and write an actual letter.

4. “The Athenaeum Portrait” of George Washington
You'll be able to spot this painting pretty easily--you've definitely seen it before. Artist Gilbert Stuart first painted George Washington in 1795. Martha Washington liked the painting so much, she asked her husband to sit for another portrait, but Stuart left the painting unfinished so he wouldn’t have to part with it. This image of Washington  appears on the one-dollar bill.

​Boston is a great city to enjoy with your friends before the big day.  It has ample opportunity for pairing libations with fun, and of course a little bit of history for our well-rounded brides-to-be!

 ​1.  Ye Olde Tavern Tours
Join us on a Freedom Trail tour where we’ll tell the story of Boston in the buildup to the American Revolution and stop at historic taverns for some local craft beer! Our tours happen in the afternoon, so get started with us and then head to one (or more) of our ideas below.

2. Drunk Shakespeare
Need I say more? Sh!t-Faced Shakespeare runs at the Rockwell Theater in Davis Square. Check here for the current lineup, but regardless of what’s showing, you won’t want to miss it! You can sip on drinks with your friends while an actor or actress gets legitimately drunker than you and your crew. Hilarity ensues, with audience participation of course! 

3. Jacques Cabaret
They say all roads lead to Jacques, so continue on after the Freedom Trail to this evening cabaret bar! They have shows seven nights a week, including Sassy Sundays, WTF Wednesdays, Throwback Thursdays, and No Filter Fridays. You can walk in or but we recommend making a reservation for a table.

4. The Donkey Show
Every Saturday Night, the Oberon in Harvard Square turns into a 70s disco to re-tell Shakespeare’s A Midsummer Night’s Dream…with a bit more gusto!  Get dressed up in club attire, disco flair, drag, or whatever is left in your suitcase to enjoy a uniquely Cambridge experience. You can join the rest of the party on the dance floor or book table seats for a more relaxed viewing. 

5. Stay Classy at a Cocktail Bar
If you’re looking for an upscale cocktail bar after too much debauchery, we recommend Yvonnes (think Great Gatsby), Lolita (think Mexican sex dungeon), or Drink (no menu, just tell the bartender what you like). 

Copp’s Hill Burying Ground is the second oldest graveyard in Boston. It was established in 1659 in the North End.  Named after shoemaker William Copp, the burying ground has many tombs of Boston’s less-affluent craftsmen and artisans. Here are some highlights to check out when you visit, perhaps as part of a day in the North End!  

1. Daniel Malcolm lived in the North End and was a member of the Sons of Liberty. He evaded paying taxes during the buildup to the Revolutionary War, but he didn’t get to see American independence, as he died in 1769. When the British soldiers occupied Boston, they’d often hang out at Copp’s Hill and use Malcolm’s tomb for target practice!

2. Puritan ministers Cotton and Increase Mather are also buried at Copp’s Hill. You may know them for their fiery role in the Salem Witch Trials of the 17th century. 

3. Robert Newman was a sexton at the Old North Church. He helped hang the lanterns during Paul Revere’s Midnight Ride: “One if by land, two if by sea…” The sea in Longfellow’s 1861 poem, by the way, referred to the Charles River, which separates Boston from Charlestown.  The British placed cannons on Copp’s Hill during the Battle of Bunker Hill, which took place in Charlestown in 1775, because it was high ground. 

4. You’ll also find the USS Constitution in Charlestown. Edmund Hartt, who was the ship’s master carpenter, is buried at Copp’s Hill. 

5. The animal life at Copp's Hill is amazing. On several occasions we've seen a black cat roaming through and bunnies (bunnies!) hiding over in the bushes by Malcolm's grave (#1 on this list).