Holes

1. Beantown Pub

Founded: 1999

Address: 100 Tremont St, Boston, MA

Historical Landmarks & Sites Nearby:

  • Granary Burying Ground: Established in 1660, this cemetery is the final resting place of Revolutionary icons like Paul Revere, Samuel Adams, and John Hancock.

  • Boston Common: Founded in 1634 as America’s oldest public park, it’s historically significant and served as a gathering place for Bostonians during the Revolution.

Funny Tidbit: The “have a Sam with Sam” tradition is likely the only chance to enjoy a cold one while honoring a Founding Father. Given Samuel Adams’ background as a brewer, it’s a fitting toast to Boston’s revolutionary history.

2. Sevens Ale House

Founded: 1933

Address: 77 Charles St, Boston, MA

Historical Landmarks & Sites Nearby:

  • Acorn Street: Boston’s most photographed cobblestone street with Colonial America charm

  • Mt Vernon Street: A lot of history’s notable figures lived here at one point including Rober Frost and Sylvia Plath. Louisburg Square is off of Mt. Veron which has always been one of the most expensive places to live in America

Funny Tidbit: It was December 5th when Prohibiton was lifted. Seven’s wasted no time and opened that same year.

3. 21st Amendment

Founded: Early 2000s

Address: 150 Bowdoin St, Boston, MA

Historical Landmarks & Sites Nearby:

  • Bowdoin Street: Named after Governor James Bowdoin, a Revolutionary leader and scientist.

  • Boston Athenaeum: A historic library founded in 1807, home to a bunch of rare books, artworks and artifacts

Funny Tidbit: Before it was 21st Amendment this spot was known as the Bellevue Men’s Club and the Golden Dome Club. JFK enjoyed a cocktail or two here back in the day.

4. Hub Pub

Founded: 1970s

Address: 18 Province St, Boston, MA

Historical Landmarks & Sites Nearby:

  • Province House Steps: Historically significant as the pathway from the State House leading to the governor’s former mansion, the Province House.

  • Milk Street: Look for the plaque noting the birthplace of Benjamin Franklin

Funny Tidbit: Hub Pub’s location on Province Street, where colonial leaders once plotted, now has people scheming over their next beer instead.

5. Mr. Dooley’s

Founded: 1991

Address: 77 Broad St, Boston, MA

Historical Landmarks & Sites Nearby:

  • Post Office Square: Formerly a maritime trading hub, now a park in the heart of Boston’s financial district.

  • Custom House Tower: When finished in 1915 it was the tallest building in the city.

Funny Tidbit: Named after a fictional, wise-cracking Irish bartender. Mr. Dooley’s character famously advised to “trust everybody, but cut the cards.”

6. Boston Sail Loft

Founded: 1984

Address: 80 Atlantic Ave, Boston, MA

Historical Landmarks & Sites Nearby:

  • Long Wharf: Boston’s longest commercial pier in colonial times, a critical point for trade and defense.

  • The Sail Loft is where the parents of Johnny Dots first shared a drink together. A Bud Light for him and Miller Lite for her.

Funny Tidbit: Long Wharf was once a major hub for smuggling in colonial Boston. Today, it smuggles clam chowder, drinks and tourists instead.

7. Black Rose

Founded: 1976

Address: 160 State St, Boston, MA

Historical Landmarks & Sites Nearby:

  • Faneuil Hall: Known as the “Cradle of Liberty,” Faneuil Hall hosted many revolutionary gatherings.

  • Old State House: Further up State Street the Declaration of Independence was read to the people of Boston in 1776.

Funny Tidbit: “Craic” is Irish slang for a good time, which is always had at The Black Rose

8. Durty Nelly’s

Founded: 1990s

Address: 108 Blackstone St, Boston, MA

Historical Landmarks & Sites Nearby:

  • Blackstone Block: Boston’s oldest commercial district, retaining the original colonial street layout

Funny Tidbit: One of the only dives in Boston where you can enter in the back and leave out the front.

9. The Dubliner

Founded: 2020s

Address: 2 Center Plaza, Boston, MA

Historical Landmarks & Sites Nearby:

  • City Hall Plaza: Known for its Brutalist architecture, City Hall is consistantly ranked in the top ugliest buildings in America. I see why…

  • Boston Sign: Located in the plaza, its the colorful Boston sign. If you didn’t know we had a city sign, then now you know

Funny Tidbit: The Dubliner celebrates Boston’s Irish heritage, where exaggerated tales and “the craic” (Irish fun) are essential ingredients to a good time.