Planning the Ultimate Historic Boston Pub Crawl

Boston is an old-time city, and it has an old-time drinking culture. Scale is the issue for anyone thinking of embarking on a pub crawl here: the areas that are most relevant for their bar history are all spread out over a city that wasn’t conceived for walking between them. Often, that distance will become part of the experience, and visitors will sample various aspects of the city as they go. A date from place to place can make an evening interesting for a couple, as they each find a new setting in which to have a conversation and connect. Often, the ride from one historic bar to another is as much the highlight as are the bars themselves. If you get the arrangement of your base wrong, you will not be on foot between stops all night. If you get out of the arrangement for your base, you will be capping the stops all night.

Pick Your Base Before You Pick Your Route

Boston’s historic drinking districts are grouped, not in concentrated areas. When it comes to colonial-era taverns and the Freedom Trail corridor, you can’t beat staying right where it all happened: Downtown or in the North End. The bars that border Boylston Street and that border the edge of the South End are more convenient along Back Bay. Compact and more pedestrian-friendly, Beacon Hill gets its reputation after just a few rounds on the steep, narrow streets. Planning a stay in a Boston hotel in these neighborhoods rather than out in the Seaport or Fenway will save you real money in ride-shares by the end of the night. For the full historic crawl, Downtown to North End is the place to be.

The Green Dragon Tavern set the Tone for Everything that followed

The Green Dragon Tavern is one of the most iconic landmarks of Revolutionary Boston. One of the most noted taverns in colonial America, the original Green Dragon in the North End was a meeting spot for figures who were part of the Sons of Liberty. While the building is gone, the current Green Dragon Tavern at 11 Marshall Street is much inspired by it and is one of the most visited attractions for people interested in Boston’s Revolutionary history. Though no longer a historical landmark like it once was, today it’s a bustling bar that offers food and beverages; it’s a must on any historic crawl because of the historic role it played in the city’s colonial history. The exposed brick, low ceiling, and enclosed ambiance are just right for an old-world feel, even in this firmly modern Boston. Come here early Saturday or Sunday evenings, as it may be very busy later in the evening.

The Bell in Hand is Widely Regarded as America’s Oldest Continuously Operating Tavern 

Opened by Jimmy Wilson, the town crier, who retired, Bell in Hand has been open since 1795. The name is derived from the ‘rounding’ bell he wore. Now it is a multi-room bar offering live music on the majority of evenings. It’s a true story, the bar is quite old, and the atmosphere is as old as the bar. The first part of the crawl is very easy, as it is a 2-minute walk from the Green Dragon. The compact distance also affords ample opportunity to experience together and makes for a convenient destination for couples seeking an easy date with a historical touch.

Plan your Route by Neighborhood, not by Chronology

The most common mistake on a Boston pub crawl is trying to connect every historic bar in the city in a single night. The Sevens Ale House on Charles Street in Beacon Hill is about 25 minutes’ walk from the Bell in Hand; Mr. Dooley’s on Broad Street is closer to the Financial District and suits a different part of the evening; The Burren in Davis Square is a genuine Irish pub with traditional music sessions but sits a T ride away in Somerville. Pick a zone and stay in it. If your zone is the North End and Downtown, you have enough material for a full night without leaving a half-mile radius. The MBTA, the city’s subway system, called the T, makes connecting to a second zone straightforward if you want to extend the evening, with the Green and Orange lines covering most of the relevant stops.

Boston’s Craft Beer Scene Rewards a Detour Beyond the Historic Core 

Boston’s serious craft beer culture has taken root around the edges of the historic core rather than inside it. Hop-forward IPAs and weekly seasonal rotation make Trillium Fort Point taproom at 50 Thomson Place at the Seaport one of the more well-regarded New England taprooms. Harpoon Brewery, on Northern Avenue, offers tours and has a beer hall near Fort Point. Both aren’t colonial era taverns, but both offer a fascinating glimpse at the Boston of today, and a combination of two or three colonial-era choices keeps the crawl from turning into a yawn.

The North End Earns a Late Stop for a Reason Beyond the Bars

The North End is Boston’s oldest residential area, established in the early 1600s, and remains one of the densest neighborhoods, featuring many narrow streets that predate the city’s 1800s street grid. Following the bars, by Boston standards, bakeries and cafes operate late in the neighborhood, and a cannoli from Mike’s Pastry or Modern Pastry on Hanover Street has become a part of the North End “ritual” itself. It is not an artificial competition; both bakeries are deserving of a visit, and you will be pleased with either one or two.

Boston’s Weather Changes What you Pack and When you go

A pub crawl in January, when temperatures drop to the single digits and the brick sidewalks ice over, is a different experience from one in October when the air is cool, and the streets are busy with leaf-peepers and college students returning to campus. Spring and fall are the practical sweet spots. The Freedom Trail Foundation website covers the historical context for much of the North End route and is a useful background if you want to understand what you are walking past between stops. Autumn festivals and university events can push up hotel prices and increase foot traffic around the city. 

The Crawl Rewards Walkers but Punishes Overplanners

When you don’t have a specific plan, you will have the best nights in Boston’s historic bar scene. The Green Dragon to the Bell in Hand is a locked opener. Thereafter, whether you’re looking to head up Beacon Hill or remain in the Downtown crowd, the night will guide you accordingly. Because the city is old, nearly all of the streets between Faneuil Hall and the State House have a layer of history. You came here to get a drink while the revolution was planned. 

Take your time to do it right, and reserve a hotel not too far off so that you can walk home. Even if you’re attending live performances, festivals, or enjoying a memorable beer tasting experience, waiting time between shows is often the most relaxing, and thus the most formative, period in an artist’s life, providing opportunities to engage in authentic dialogue and shared experiences. Whilst planning the event itself is an important component of a great night out, the space around an event can have as much impact as the event itself, so planning the event space is important too.