The Ultimate Rock and Roll Weekend in Boston

Before you go

Two Days in Boston

Day 1

Morning: Wake up and rock out

• Find your nearest Pavement Coffeehouse for a pour over and house-made bagel. The iconic local roasting company has eight locations around town, each of which serves the brand’s fantastic coffee. The house blend, Rathskeller, is named for a legendary bygone rock club.

Midday: Learn from a local musician

• Check out Soundscape Tours, a 90-minute excursion led by a local musician, who will take you past major landmarks and pepper you with facts and stories. You’ll hear about the Boston connection to bands like The Police and Pixies, get acquainted with the Fenway area, and end up at a record store.
• When you’re hungry for brunch (or linner), head to Shy Bird. The day-to-night menu spans honey-Sriracha chicken and waffles, vegetarian grain bowls, and small plates like pork belly lettuce wraps or marinated anchovies. It has espresso, cocktails, and a lively patio, too.

Afternoon: Spend some peaceful time with fine art and flowers

• The Museum of Fine Arts is a quiet yet stimulating place to spend as many hours as you can. If you visit before June 22, make sure to see the Art of John Wilson. It’s the first major show celebrating an influential artist from Boston’s historically Black Roxbury neighborhood.
• In the summer, the James P. Kelleher Rose Garden is in full bloom. It’s a small rose garden near the museum that’s perfect for a fresh air stroll, or use it as the beginning of a larger exploration of the Emerald Necklace park system.
• Stretch your legs with a walk on the Charles River Esplanade, a narrow park along the water between Boston and Cambridge. Maybe you’ll catch a free concert or dance class at the Hatch Shell, a historic outdoor performance venue. And even if there isn’t anything going on, the Night Shift Beer Garden is open through the summer.
• When the time you may know as “happy hour” approaches, I regret to inform you that you’ll be paying full price for your drinks. Boston doesn’t have happy hour, but we do have delicious oysters. Eventide Fenway does buy-one, get-one trays of oysters every day from 3 to 6 p.m.

Evening: Catch a concert, or maybe a home run ball

• If you’re in town while the Sox are playing, catching a Red Sox game at Fenway Park is an unmatched experience, if only to hear organist Josh Kantor in action—and he takes requests. If the Sox aren't playing, check the concert calendar for major stadium bands like The Who or My Chemical Romance.
• Or, see what’s playing at one of Boston’s best mid-size music venues. MGM Fenway Music Hall and House of Blues are both on Lansdowne Street, while Roadrunner—my personal fav for sightlines, sound, and beer selection—is in nearby Brighton.
• Dinner depends on your evening activity. In Fenway, stay at Eventide for the brown butter lobster roll. In Brighton, try the taproom and kitchen by Widowmaker Brewing. This casual place has a metal sensibility, elite lagers and hazy IPAs, and a solid version of South Shore-style bar pizza (itself a paragon of Boston-area culture).

Day 2

Morning: Browse one of Boston’s lovely pedestrian-only streets

• Before heading to Camberville, take a minute to stroll Newbury Street. The mile-long corridor between Massachusetts Avenue and the Public Garden is pedestrian-only on certain days, and it’s lined with art galleries, cafes, and stores. Newbury Comics has a well-stocked record selection in the basement level of its eponymous location. Among the many fine art storefronts, Arden Gallery displays a colorful and diverse collection of art by international artists.

Midday: Check out some English muffins and Continental art

• When you’re ready for brunch, take the Green Line to Union Square, and then pop a couple blocks over to Somerville’s Vinal Bakery. The English muffins make the best breakfast sandwiches (I love the one with dijonnaise and garlicky greens). If you’re arriving after 11 a.m., next-door deli Vinal General Store has fun flavors of soft serve ice cream.
• For some cultural enrichment, make your way to the Harvard Art Museum, just outside of Harvard Square. It’s free to visit with dozens of galleries across three floors; through July 27, special exhibit Edvard Munch: Technically Speaking shows more than 70 works, demonstrating the Norwegian artist’s playful, experimental approach to painting and printmaking.

Afternoon: An indie market with a killer record store

• Back in Union Square, Bow Market is an outdoor courtyard and indie marketplace festooned with public art. Get lunch from Saus, a vegetarian burger-and-fry specialist; or Nibble Kitchen, which platforms aspiring restaurateurs. Then spend the afternoon browsing the market’s mix of small bars and retail shops. Don’t miss Vinyl Index, a boutique record shop that has an in-store bar, founded by prominent Boston DJ George Andrinopoulos, also known as 7L. Weekends at Bow see frequent public events like DIY screen printing, comics workshops, yoga, and more, so give the schedule a glance.

Evening: Hit a rock venue and get some classic New England cuisine

• Field & Vine is cozy and cool for a memorable dinner. Co-owners Sara Markey and chef Andrew Brady match fresh takes on New England cuisine with funky, food-friendly wine. For a slightly more casual setting, try sister spot June Bug for wood-fired sourdough pizza.
• Later, head to Somerville Theatre for live music or a movie. The art deco cinema brings local and indie films to Davis Square, as well as performing artists like Ani DiFranco. Upstairs, the Crystal Ballroom is a rock club with shows by local and touring bands.

Late-night: Cap off the trip at a film-famous pub

• Check out Somerville’s new Tall Order Bar for a midnight snack. The lived-in pub, which also appeared in The Social Network, has been reinvented by a pair of renowned local bartenders. For an ideal nightcap, order a pile of rosemary fries dusted in gouda and the low-proof sherry martini, Little Panda.

If you have three days

All of the above, but add...

• Walk the halls and gardens of Isabella Stewart Gardner Museum, a palatial Fenway mansion turned into a world renowned art gallery. There are multiple exhibitions on at any given time, they host regular public programs like garden tours and musical performances, and the courtyard garden is always in bloom.
• Take the Green Line to Brookline for lunch at Stoked Pizza Co., which happens to be co-owned by Letters to Cleo bassist Scott Riebling. The ’80s pizza party aesthetic and fun soundtrack of the place set a welcoming vibe—as do the ample vegetarian and vegan options on the menu.
• Wind down the weekend inside a loud venue on Commonwealth Avenue, the intimate Paradise Rock Club. It’s been open since 1977 and has hosted countless artists while they were still on their way to the top, from U2 on its first American tour to Anderson .Paak in 2016.