Boston, MA

Go For: Arts & Culture, History

From Poughkeepsie: 3 hours, 45 mins

With its stately Federal-style architecture, rich history, and urban vibes, Boston is worth a visit any time of year, but the city puts its best foot forward in the fall, with cultural offerings and rich autumnal color. Carve out some time to walk in the footsteps of our nation’s founding fathers along the Freedom Trail. The 2.5-mile walk heads past major landmarks, like Old North Church, Faneuil Hall, and Granary Burying Ground, where Samuel Adams, Paul Revere, and John Hancock were laid to rest. Stroll through Boston Common (and keep an eye out for the beloved Make Way for Ducklings statue), the country’s oldest city park, which comes alive with fall color in mid-October. Afterward, cross the Charles River and spend an intellectual afternoon in Cambridge, discovering the preppy shops, cozy coffee spots, and trendy restaurant scene.

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Photo credit (L to R) Kyle Klein, Joyelle West, marco borggreve

In the Back Bay neighborhood, seek out masterpieces — Renoir’s Dance at Bougival, Rembrandt’s The Artist in His Studio, and canvases from Monet’s Rouen Cathedral series — among the 500,000-work collection at the Museum of Fine Arts. Just a couple blocks away, the Isabella Stewart Gardner Museum (designed in the style of a 15th-century Venetian palazzo; it’s a work of art in itself) is known for its collection of big-name European artists — and for an infamous unsolved 1990 art theft.

For dinner, artistry makes it way onto the plate (and into the cocktail glass) at New England brasserie Townsman. Meanwhile, the succulent 100-day-aged rib-eye at Grill 23 seems like just the ticket before a night of classical music. Don’t leave town without a visit to the Boston Symphony Orchestra, which performs in (what else?) a National Historic Landmark.

STAY: XV Beacon

Housed in a 1903 Beaux Arts building in the upscale Beacon Hill neighborhood, XV Beacon seamlessly blends Boston’s heritage with its modern sensibilities. Take, for example, the sleek black-and-gray lobby, where zebra-print rugs share space with Benjamin Franklin busts and Ancient Roman mosaics. Original glass-encased elevators escort guests to rooms with Federal-style columns, brushed stainless-steel fireplaces, cashmere blankets, and fragrant bath salts to soothe achy muscles after a day walking Boston’s cobblestone streets (no wonder it was voted the top hotel in the US by Condé Nast Traveler readers in 2014). Once you’ve seen the city from the roof deck (didn’t we mention that yet?), call for the complimentary chauffeured Lexus service and get whisked across the city in style. From $525/night;

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