Off-the-Freedom-Trail Boston

Travel time: Four and a half hours from NYC by bus

Why go: The hulking elevated expressway that once sliced through Boston and blighted its waterfront has been replaced with a string of green spaces, and cultural offerings have been boosted by the Institute of Contemporary Art (icaboston.org) and the new Art of the Americas Wing at the Museum of Fine Arts, Boston (mfa.org).

Stay here: The Ames Hotel is in a landmark 1889 building, but the inside was designed by David Rockwell. 1 Court St at Washington St (ameshotel.com). Rates start at $255. Mention TONY, or enter promo code SPTONY, for 20% off through June 5.

Do this: Follow the Rose Kennedy Greenway (rosekennedygreenway.org), a mile-long chain of parks planted in the footprint of the old expressway. At the North End, glimpse the futuristic 2002 Zakim Bridge, then head south alongside the developing waterfront. Dotted with fountains and public art, the Greenway is served by 12 food trucks, and this summer it debuts the Greenway Open Market (Saturdays, July 9--Sept 17; greenwayopenmarket.com). At Northern Avenue, cross the bridge to Fan Pier and the dramatic, glass-walled Institute of Contemporary Art. Nearby, Fort Point Channel is a longtime artists' live-work district—browse a selection of local creative output at Made in Fort Point (617-423-1100). Although the binannual Boston Cyberarts Festival has largely logged out until 2013, you can still catch "Fluid Perimeters: An Exhibition of Dynamic Digital Imagery" at the new Atlantic Wharf development (290 Congress St at Fort Point Channel; bostoncyberarts.com/festival) through April 2012. Jamaica Plain's Axiom (141 Green St at Armory St; 617-676-5904, axiomart.org), attached to Green Street subway station, is at the center of Boston's new-media and video art scene. JP's low-rent Victorian houses have drawn a young, arty crowd for decades, but the neighborhood now has enough to tempt out-of-towners. Shops and galleries cluster on South Street, including one of the city's best vintage shops, 40 South Street (40 South St between Sedgwick St and Carolina Ave; 617-522-5066, fortysouthst.com).

Eat here: In Fort Point, grab a slow-roasted veal panino at James Beard Award--winning chef Barbara Lynch's sleek Italian diner Sportello (348 Congress St at A St; 617-737-1234, sportelloboston.com). Some of the city's freshest food concepts reside in Jamaica Plain. Snack on a superb tortilla espaola ($4) at tapas bar-shop combo Tres Gatos (470 Centre St at Roseway St; 617-477-4851, tresgatosjp.com) before browsing books and records in the back.

Find more restaurants, shops and things to do at timeoutboston.com.