Cambridge and Somerville: start in Central

Do Central Square. It is the most compact of the three routes, it has live music most nights, and it is on the Red Line. Harvard to Inman and Union to Davis are the backups, and each route has a music stop, a drink stop and a food stop, so nobody has to drink much.

One thing to cross off older lists: Cambridge Brewing Company in Kendall is closed, per its own site. The company says it has been in craft beer since our inception in 1989, and you can still find its beer on tap elsewhere. Also, Union Square is on the Green Line Extension, not the Red Line.

Why Cambridge bars are a different animal

Cambridge is a city that argues with itself about drinking, and it has for a long time. Harvard Magazine says the city first voted to ban alcohol sales entirely in 1886. It says Cambridge then remained a dry city for 47 years, until Prohibition's repeal. The magazine adds that patrons crossed the river to drink in Boston, which is the oldest version of a pub crawl that ends in the wrong city.

The argument is current. This summer, the magazine reports, bars in Cambridge could stay open until 3 a.m. for six weeks. The License Commission also approved six public drinking zones in major squares. Before any of that, a May draft of new city rules had proposed no alcohol sales in the last hour before closing. By the June 30 draft, the magazine says, the wait-period and last-call rules were struck.

The loosened rules were popular with the bars. The magazine counts nearly 40 bars and restaurants that began offering to-go drinks. The hours were an experiment, so do not plan around them.

What that means for a Saturday: the extension was temporary and the draft rule is gone, so the posted hours at each door are the only hours that count. We treat every closing time below as a license term, not a promise. For where the 2 a.m. default comes from, see why Boston closes at 2 AM.

Route 1: Central Square

Four stops, no transit between them.

• Drink: Brick & Mortar lists Thursday and Friday 3pm to 1am. Saturday runs 5pm to 1am. Earlier in the week it lists Monday, Tuesday, Wednesday 3pm to 12am, so a Tuesday here ends an hour earlier than a Friday. Start here.
• Music: The Middle East is really several smaller live venues under one roof, so check which room your ticket is for. Eat first, because the advice is to grab some food before the show.
• Pub: The Plough and Stars has live music Monday through Saturday from 10:30 pm. It also has weekend afternoon sets. It has been going since 1969. It is the easiest late stop on the list.
• Dance: Phoenix Landing was listed as a club open every night till 2am. That listing is old, so confirm before you walk over.

Two of these stops share one street. Brick & Mortar lists 567 Massachusetts Ave as its address. The Plough lists 912 Massachusetts Ave. as its own. That is the case for doing Central as a walk along one avenue.

Route 2: Harvard Square to Inman

Food first, then music.

• Eat: Russell House Tavern on JFK Street has a big bar and lists Friday hours of 11am to 1am. Its site also advertises oysters during late-night shucking hours. Those run Sunday to Thursday from 9pm to 11pm. On weekends they run Friday and Saturday from 10pm to 12am. On Friday the shucking ends at 12am, an hour before the bar's 1am close, so treat it as the last food call.
• Drink: The Longfellow Bar at Alden & Harlow sits above Alden & Harlow and makes its own infusions, vinegars, syrups and bitters. Order the cocktail that uses them.
• Music: The Sinclair is a bi-level room with a balcony.
• Finish in Inman: The Lilypad holds just 80 people, so check the lineup and get there early. It is a bus or a taxi from Harvard rather than a stroll.

Route 3: Union Square to Davis Square

Two squares with a short ride between them.

• Beer: Aeronaut Brewing Company is a brewery and taproom near Union Square. Remnant Brewing is a brewery in Bow Market. It says it opened in 2018 in the heart of Union Square. Check each site for current hours.
• Cocktails: Backbar is tucked in an alley and runs Wednesday through Sunday. It takes no reservations. It also has only 39 seats, so go early or expect to wait. Its home page lists last seating at 11:15pm, so this is the stop for the start of the night, not the end of it. Its own site says Boston Magazine rated it the number one bar in Boston in March 2020, which is a self-reported honor.
• Music: The Burren in Davis Square advertises live music 7 days a week. Use it for the finish.

The order matters on this route. Cocktails go first and the Burren goes last.

Getting home

Central, Harvard and Davis are Red Line stops. Here are the MBTA pages for Central. Davis has its own. And Union Square is on the Green Line Extension. Late service differs by line, so check Last Train before the final stop, and see getting home after last call for backups. Pick the stop you will leave from before you pick the last bar, and leave with the people you came with.