A strong line of history, from the Revolutionary War to the 20th-century counterculture, can be traced through Inman Square, which doesn’t get the attention it deserves compared to better known “big-name” squares such Harvard, Central and Kendall. The neighborhood punches well above its weight in all departments and is well worth seeking out by bike or by foot—sadly, the streetcars left around 1950, conferring upon Inman Square an insular, best-kept-secret kind of vibe.
Jay Leno made his first stage appearance here (at Ding Ho restaurant, now Ole), there’s a lively undercurrent of Brazilian and Portuguese culture, and for a flavor of the 1970s underground, seek out the occasional alternative walking tours led by local librarian and historian Tim Devin.
Where to Eat
You’ll find an extended translation of the name Momi Nonmi on the restaurant’s website—it has to do with love of drinking and Hawaiian pearls—but it all amounts to a first-rate modern izakaya (Japanese pub). Oleana is never less than a taste-bud revelation, rooted in Middle Eastern flavors, with one of the city’s most delightful warm-weather patios, and Punjabi Dhaba is a superior curry house, pitched as an Indian roadside cafeteria.
Where to Shop
Practice Space is an “artist-run, women-run” studio that serves as a studio for contemporary art across a variety of platforms, and also has a shop full of amazing art supplies, zines, textiles, ceramics, clothes and more. For fine booze, look no further than Inman Square Wine & Spirits which hosts regular, cleverly curated tastings and keeps tabs on the latest notables on the local craft beer scene.
Where to Drink
Southern-inspired comfort food, cold beer and neo-mid-century kitsch have made a lascivious pact at Trina’s Starlite Lounge, where the brunch cocktail list includes the Somerville Speedball and the Zickleback shooter. Bukowski Tavern, a brother to the twin location in Back Bay, channels the spirit of Angeleno literary barfly Charles Bukowski into a heady combination of hearty fare and tongue-in-cheek “surly service” while The Thirsty Scholar has no real need to trade on its movie history as a memorable location in “The Social Network”—it’s actually a top-notch pub in its own right.
If a hub for experimental music improvs, poetry readings and avant-garde film screenings is absent from your radar, look no further than Outpost 186, which hosts all manner of underground creative alchemy. Founded in 2005, The Lilypad plays a similar role, with the focus on music and art—performers during the fall include the Allan Chase Quartet and Jenny Lin.