How To Spend a Long Weekend in Gay Boston

New England’s largest city offers urban elegance washed in the spectacular beauty of autumn

The iconic DeLuca's market on Charles Street, recently reopened after a devastating 2010 fire.

Philadelphia and Boston have a lot in common: Both are sprawling East Coast cities with unpar­alleled historical roots, boast a beefy population of Ivy League heartthrobs, and are situated a mere hop, skip and a swish away from two of the gayest beaches in the nation. There is one time of year, however, when Beantown has a slight edge on us: autumn. Even with the best of New England at its doorstep, Boston, with its enchanting tree-lined streets and parks, holds its own as a primo destination for queens wishing to go leaf-peeping without straying too far from the comforts (and gay-friendliness) of a modern city. 

The stately XV Beacon.

I felt more than welcome at XV Beacon, a stately boutique hotel that, well, beacons gay guests with a décor that tastefully showcases the building’s 110-year history while still offering 21st-century perks: gas fireplaces, heated towel racks, Italian white-marble bathrooms with rainforest showers. There’s even a complimentary in-house driver ready to tote you anywhere within city limits—in a Lexus.

Around the corner is Boston Common, an ideal entry point to the “Emerald Necklace,” a pristinely maintained, 1,100-acre chain of parks designed by Frederick Law Olmsted, the man behind FDR Park. Rent a two-wheeler from Hubway and pedal the seven-mile path that crosses the entire city. You’ll ride over charming stone pedestrian bridges, past lily-padded lagoons and, eventually, find yourself deep in a red-,yellow- and burnt orange-leafed forest.

Point your spokes toward Tremont Street in the South End for the true gay-Boston experience. Here, you’ll find legendary bars like Boston Eagle and Club Cafe, and the best gay-watching in the city at popular brunch spots Tremont 647 and Francesca’s Espresso Bar. If shopping is on your agenda, Back Bay’s Newbury Street is the promenade.

Park view from a stop along the Emerald Necklace.

Boston is also one of the nation’s premier cultural hubs: Highlights this fall include an exhibition of watercolors from John Singer Sargent at the Museum of Fine Arts, and cellist Yo-Yo Ma performing with the Boston Symphony. (The Philadelphia Orchestra’s Charles Dutoit guest conducts in November.) Get your tickets early.

On your last night, save room for dinner at Mooo.…, the opulent steakhouse inside XV Beacon, then mosey up to the hotel’s rooftop deck with a nightcap. Standing under the Boston sky, you might not get the romantic starry-night view you’d find in, say, rural Vermont or New Hampshire. But faraway twinklers are a small price to pay for the luxury of having the best of both worlds at your fingertips—right where they belong.

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