The Ultimate Boston Pub Crawl: 6 Must-Stop Spots Starting in Beacon Hill

Boston is a city built for pub crawls — with its historic streets, walkable neighborhoods, and a pub (or three) on nearly every block. Whether you're visiting for the weekend or rallying the crew for a night out, this Boston pub crawl guide will take you from cozy pints to rooftop vibes — and it all starts at one of the best bars in Beacon Hill.

Stop #1: Cheers Boston – Beacon Hill

Start your night where charm meets character. Tucked into the cobblestone streets of Beacon Hill, Cheers is the quintessential Boston bar: warm, welcoming, and where everybody knows your name! Whether you're grabbing a local draft, sipping a whiskey, or kicking things off with shareable apps, this is the ideal launchpad for your crawl.

What to Order: A pint of Harpoon IPA or our bartender’s rotating local pick, paired with our crispy wings or cheesy nachos.

Stop #2: The Sevens Ale House – Charles Street

Just a short stroll away, this no-frills neighborhood pub is a local favorite. Dive into a classic beer selection, old-school dartboards, and that lived-in vibe that makes you want to stay longer than you planned.

Stop #3: Night Shift Lovejoy Wharf – West End

Time to switch things up with a modern taproom experience. Night Shift offers an impressive variety of house brews — from hazy IPAs to crisp lagers — plus a scenic view of the Zakim Bridge if you’re lucky enough to grab a window seat.

Stop #4: Banners Kitchen & Tap – Near TD Garden

Sports bar meets beer hall. With dozens of beers on tap and massive screens, Banners is the place to regroup, rehydrate (or not), and keep the momentum going. Bonus: it’s a great stop for a round of shots if your group needs a boost.

Stop #5: Democracy Brewing – Downtown Crossing

Head downtown for this worker-owned brewpub that’s making a name for itself with bold beer and even bolder mission. The tap list changes often, but their flagship Worker’s Pint is always a solid choice.

Stop #6: Trillium Garden on the Greenway (Seasonal)

Cap off the crawl under the stars with one of Boston’s most beloved breweries. If it’s spring through fall, Trillium’s outdoor beer garden is a magical last stop. Sip a juicy double IPA, soak in the skyline, and toast to a successful crawl.

Pro Tip: This crawl is best done Thursday through Saturday. Stay hydrated, tip well, and pace yourself — Boston is best enjoyed with friends and plenty of laughs.