1. Where to Stay
Splurge on one of 114 handsome minimalist rooms and suites at the Ames Hotel (from $395), which opened in 2009 in a stately Romanesque building built in 1893. It’s located just a few blocks from the harbor and the bustling Fort Point neighborhood, and the hotel houses a sceney in-house tavern, Woodward, where D.J.’s spin on Friday and Saturday nights until 2 a.m.
Trade space for style at Hotel Veritas (from $195), which opened on Harvard Square in 2010. The 31 rooms are small, averaging around 230-square-feet, but the details—understated Deco-style furnishings, Anichini linens, and Etro bath products—up the comfort factor.
Get a great deal at Hotel 140 (from $99), where 55 basic but immaculate rooms are just steps away from some of the Back Bay’s poshest five-star options—as well as Copley Square and the city’s destination shopping streets, Newbury and Boylston.
2. Where to Eat
Boston arrived late to the food-truck party, but this year the city is swarming with mobile dining options. Bon Me, the winner of last year’s first-ever, citywide Food Truck Challenge, serves bánh mi ($6) alongside build-your-own rice bowls and noodle salads topped with barbecued pork, spice-rubbed chicken, or tofu ($6) and tea-marinated deviled eggs ($2) from a former DHL delivery van.
Track down Boston’s only mobile gastropub, Staff Meal, the love child of two classically trained, snout-to-tail-minded chefs. Several items fall somewhere between entrée and dessert, like baklava layered with foie gras and pistachios, and bacon-fat-fried pound cake ($4 each), while the sandwiches are similarly decadent; recent choices included a Korean-style bibimbap made with braised pig’s feet, rice, and kimchee ($6).
Try vegetarian street cuisine at Clover Food Lab, which has multiple trucks stationed around the city and uses locally sourced produce in its menu of creative meatless fare. Top marks go to the chickpea fritters—lighter and crunchier than falafel, served with pickled red cabbage, carrots, and housemade tahini ($6)—and to the barbecued seitan sandwiches, stuffed with carmelized onions and melted cheddar ($5).
3. What to Do
Don’t miss Anthropocene Extinction, the new exhibit at the Institute of Contemporary Art ($15) by Brooklyn-based street artist Swoon. Since the early aughts, Swoon’s intricate paper cut-outs and gorgeous wheat-pasted portraits have decked the walls of derelict warehouses in the five boroughs; here, her massive installation takes over much of the museum’s ground floor (through December 30).
Explore the city on two wheels using the newly unveiled Hubway, a bike-share program with 600 bicycles stationed at 60 different stations. Hiring one of the New Balance three-speed bikes costs just $5 per day; you can pick one up at any station, swipe your credit card at its kiosk, and drop the bike at any other station when you’re done. Route maps and multiday pricing are available, too.
Stroll through the mile-long ribbon of public parks and green spaces collectively known as the Rose F. Kennedy Greenway. The parks, which occupy the space once used by the city’s central expressway (the “Big Dig” moved it underground in 2007), begin in the North End and snake alongside the Wharf District down to Chinatown. All are WiFi-accessible, surrounded by gardens and urban horticulture projects, and dotted with sculptures and fountains.
4. Insider’s Tip
Venture away from the city’s traditional boutiques and head to the SoWa Open Market (short for “south of Washington Street”), open Sundays through October 30. Here, the eclectic wares offered by dozens of local vendors have a homegrown, DIY vibe. Haberdash Vintage, for example, sells one-of-a-kind vintage frocks, shoes, and bijoux out of a shiny 1954 Bellwood trailer. And Black Sheep Designs offers delicate jewelry made from antique keys, coins, and other found materials.
5. Oddball Day
Head to Cambridge’s M.I.T./Kendall Square neighborhood for a day of free cultural pursuits. Take the T to Kendall Square to see Paul Matisse’s musical sculpture Kendall Band, which hangs between the train tracks and was recently refurbished by a group of M.I.T. engineering students. Next, grab coffee and house-baked breakfast pastries—like mini cinnamon rolls ($1.50 for 3), maple-bacon bread ($2.25), or craquelin (sugar-cube-stuffed brioche, $2.50) at Area Four. Next, walk to M.I.T.’s Frank Gehry–designed Ray and Maria Stata Center, an architectural cluster of haphazard-looking angles and metallic surfaces. Midday on weekends, you’ll likely see members of local parkour group Hub Freerunning acrobatically vaulting, scaling, and balancing around the building’s central courtyard. Hub members welcome drop-ins at their “jams,” as well as watchers (those interested in learning from them can sign up for Parkour 101, a class that founding traceurs Dylan Polin and Curran Ferrey regularly lead at the Boston Center for Adult Education). Spend another hour or two on campus, wandering among the many public art installations (by Alexander Calder, Henry Moore, and others), and check out the free exhibits at the List Visual Arts Center (Lichtballett, Otto Piene’s light-based sculpture installation, opens October 20). Then head back to Kendall Square for upscale Southern-fried cuisine at Hungry Mother (try the crispy-duck-and-hominy stew, $12, with a side of country ham biscuits and red pepper jelly, $5). Finish the night by choosing from 100 beers on tap at newly opened brew emporium Meadhall.
For news about street happenings—flash mobs, guerrilla pranks, free events—check out the site for Societies of Spontaneity.
For calendars of nightlife, music, and art events, and reviews of the city’s restaurants and bars, check out the Boston Phoenix or pick up a print copy.
The Improper Bostonian’s style-minded features cover local bands, sports, fashion, and parties.
Tune in to what cool Bostonians are listening to by streaming WFNX, one of the East Coast’s first alternative radio stations.