Annapolis Maryland Gay Scene Guide

Main Street Annapolis

Annapolis and Anne Arundel County Conference and Visitors Bureau

Maryland's capital city, historic Annapolis is situated on the west shore of the largest estuary in the United States, Chesapeake Bay, and is sometimes compared with Newport, Rhode Island, and Charleston, South Carolina among the East Coast's leading hubs of boating, colonial seaport architecture, and nautical charm.

Annapolis is located at a key section of Chesapeake Bay, where the Bay Bridge (U.S. 50) crosses the bay and connects the metro Baltimore-DC region with Maryland's and Delaware's Eastern Shore. Many gay and lesbian tourists pass through Annapolis en route from Baltimore and DC to the DelMarVa Peninsula's favorite gay ocean resort community, Rehoboth Beach, Delaware, which is about a two-hour drive due east of Annapolis. Baltimore is 30 miles north via I-97, and Washington, DC is 35 miles west via U.S. 50.

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Annapolis Maryland Gay Guide

The downtown Annapolis waterfront

Trip Savvy / Andrew Collins

Annapolis is one of the oldest though least-populous (with 39,000 residents) state capitals in the country. Its blue-blood yachting culture and it's being home to the scenic and historic campus of the U.S. Naval Academy may give some the impression it's a rather conservative city, but as the hub of politics in an increasingly progressive state, which legalized gay marriage at the beginning of 2013, Annapolis is quite diverse politically and very GLBT-welcoming on the whole - the city hosts the Annapolis Gay Pride Festival each year in early August. Other popular Annapolis annual events include the Annapolis Spring Sailboat Show in April and the Annapolis Arts and Crafts Festival in June.

Annapolis is home to a handful of gay-owned historic B&Bs in the center of town, along with a slew of charming restaurants and bars, none with exclusively gay followings, but most with a mixed clientele. (Nearby Baltimore and Washington, DC have sizable gay nightlife scenes if you're looking for a night of clubbing.) As a destination for gay travelers, this compact, hilly city sculpted by bays, inlets, and frontage along the Severn River makes for a lively, enchanting, and culturally rich weekend getaway, especially given its close proximity to Baltimore and DC, as well as one of the Mid-Atlantic's largest airports, Baltimore-Washington International (BWI), just 25 miles away.

No visitor to Annapolis should miss a stroll around the elegant campus, known as "The Yard," of the U.S. Naval Academy, which was founded in 1845 and enrolls about 4,600 Midshipmen, about 20% of whom are women ("Midshipman" is the term for students, regardless of gender). Now that gays and lesbians may serve openly in the U.S. military, the U.S. Naval Academy has developed and active and cohesive LGBT group, USNA Out; there's actually a long if quiet history of LGBT persons affiliated with the Naval Academy and the Navy itself, with some speculating that early-19th-century U.S. Naval war hero Stephen Decatur had a romantic affair with fellow naval officer Richard Somers. The Academy campus makes for a lovely stroll - Admission is free, but you must present a valid ID (such as a diver's license) to enter the grounds. On campus, be sure to visit the exceptional USNA Museum in Preble Hall, which contains exhibits documenting the nation's extensive and storied naval history, and an upper-floor gallery of model ships.

Just beyond the campus, which overlooks the Chesapeake Bay, downtown Annapolis abounds with colonial architecture and is said to have more 18th-century buildings than any city in the country. A number of old homes are open to the public as museums, including the William Paca House & Gardens, the Hammond-Harwood House, and the Banneker-Douglas Museum, which interprets Maryland's rich African-American legacy. There's also another ancient and venerable educational institution in downtown, historic St. John's College, the third-oldest post-secondary school in the nation (which has a second campus in Santa Fe, New Mexico.

Also worth a tour is the Maryland State House, which dates to 1779 and served briefly as the first peacetime capitol of the United States - it's the oldest statehouse in the country still in legislative use, and tours are available daily.

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Annapolis Gay-Friendly Hotels Guide - Annapolis Historic Inns and B&Bs

photo by Andrew Collins

Annapolis has a wide variety of hotels and inns, from upscale, contemporary chain properties to distinctive, gay-owned B&Bs. Among high-end hotels, the striking, contemporary Hotel Annapolis (126 West St., 410-263-7777) is a handsome red brick beauty with 234 posh suites and rooms, one of the best destination restaurants in the city, BarOak, and easy proximity to the Maryland State House and the city's prime retail and dining areas.

About a half-mile farther west, the Westin Annapolis (100 Westgate Circle, 410-972-4300) is another attractive, upscale option with roomy accommodations, a beautiful indoor pool, and an impressive fitness center. Directly overlooking the waterfront and a 10-minute walk from the U.S. Naval Academy as well as the bustling dining scene across Spa Creek in East Port, the Marriott Annapolis Waterfront (80 Compromise St., 888-773-0786) has recently completed an ambitious renovation; many rooms have views of the bay and USNA "Yard", and Pusser's Caribbean Grille is a fun, waterfront-facing venue for a meal or cocktails.

Among smaller properties, the gay-owned Annapolis Inn (144 Prince George St., 410-295-5200) is decadently opulent three-suite B&B across the street from the U.S. Naval Academy "Yard" and a few steps from the restaurants and shops of Main Street. Accommodations are splendidly furnished with romantic, sweeping drapes, fine imported Italian linens, stunning bathrooms with towel warmers and marble accents, spacious sitting areas, and - in two suites - wood-burning fireplaces. Breakfast is a leisurely three-course affair. This refined retreat is ideal for a special occasion.

Set in a red brick townhouse in the downtown historic district, another gay-owned lodging option is the Two-O-One Bed and Breakfast (201 Prince George St., 401-268-8053), whose owners Graham and Robert take pride in preparing impressive breakfasts each morning and sharing details about the inn's meticulous gardens and fine antiques. There are four rooms and suites, including two with a double Jacuzzi tub.

Just steps from the Maryland State House, charming Chez Amis B&B (85 East St., 410-263-6631) is is another stylish and intimate option. Hosts Elly and Joe Tierney are friendly and knowledgeable, and the four rooms and suites in this handsome 1880s building are gorgeously appointed, with country French flair - the State House Room has superlative views of the building for which it's named. A lavish three-course breakfast is included.

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