Maryland's Eastern Shore Gay Guide - Talbot County, Maryland & Environs

Although GLBT visitors to the DelMarVa (Delaware-Maryland-Virginia) peninsula typically flock to the summer beach getaway of Rehoboth Beach, which is indeed a festive place for sunning on the sand, partying at gay bars, and shacking up with buddies in vacation rentals and gay-owned guest houses, Maryland's Eastern Shore has quite a lot to offer, especially if its romance and a lower-keyed pace you're after. Now that Maryland has gay marriage, quite a few same-sex couples have begun looking to this expanse of country farms, historic boating communities, and small cities that separate Chesapeake Bay from the Atlantic Ocean. In particular, the region's very central Talbot County has developed an increasing gay following.

The Eastern Shore is made up of nine counties, extending from the very top of the bay (and state) in Cecil County down Kent, Queen Anne, and Caroline counties (which border Delaware to the east), and on further south through Talbot, Dorchester, Wicomico, Somerset, and Worcester counties, to the Virginia border. It's a large area, and you can gain a good sense of the whole area by reading the Visitors Guide to the Eastern Shore of Maryland, by Rachel Cooper, the Guide to Washington, DC. For this gay guide to the region, the focus is primarily on a few towns in the area (mostly around the midsection of the peninsula) with a particularly strong following with the LGBT community, or notable accommodations popular with the gay market. These include the towns of St. Michaels, Tilghman Island, Oxford, Easton, Cambridge, and Salisbury (and vicinity), but you'll also find information on some other gay-friendly inns set around the region, and a bit on the popular beach community, Ocean City, which is a friendly and scenic town but with not much in the way of a gay scene, in part because Rehoboth, Delaware (just 25 miles north) is such an LGBT mecca.

01 of 02

Getting There

photo by Andrew Collins

You can reach the Eastern Shore via a few key routes. The region is particularly popular with residents of Washington, DC, and Baltimore; from this area, it's about a 90-minute drive via Annapolis and U.S. 50 over the Chesapeake Bay Bridge (it's the same route you'd take from these cities to Rehoboth). If you're driving here from points north, take I-95 south to Rte. 1 (toward Christiana, Delaware, just south of Wilmington), and follow this road south to Middletown, then Rte. 299 west to U.S. 301 south, which leads into Maryland and continues south toward the center of the peninsula - from Philadelphia, it's about a two-hour drive to Easton. Finally, if driving up to the Eastern Shore from Virginia, take U.S. 13 from Norfolk-Virginia Beach north through the Chesapeake Bay Bridge-Tunnel and follow it north up the peninsula; from Norfolk, it's a 3.5-hour drive to Easton (and just a 2.5-hour drive to Salisbury).

Tourism Information on Maryland's Eastern Shore

The Eastern Shore has no single tourism office, but at the Eastern Shore section of the Visit Maryland website, you'll find links to the Caroline, Cecil, Dorchester, Kent, Queen Anne, Somerset, Talbot, Wicomico, and Worcester county tourism offices.

Continue to 2 of 2 below.
02 of 02

St. Michaels Gay Guide - Weekend in St. Michaels, Maryland

photo by Andrew Collins

Long synonymous with yachting and maritime history, including the role the town played cleverly fending off a British attack during the War of 1812, St. Michaels is situated along a narrow neck of land that extends west of Easton (the seat of Talbot County) along the Miles River, into Chesapeake Bay. Although only about 1,000 residents live in this colonial village year-round, the downtown area does have a nice selection of sophisticated boutiques, cafes, and B&Bs and is also home to the fascinating Chesapeake Bay Maritime Museum, which overlooks the bay, offers boat rides and boat-building demonstrations, and some terrific exhibits on local wetland ecology, and the region's illustrious shipbuilding history.

A romantic, upscale community that you may recognize from its having been featured prominently in the film The Wedding Crashers, St. Michaels has long been where Washington, DC bigwigs sneak away for weekend R&R (many have second homes here). As a vacation destination, the town is most famous for one of the Mid-Atlantic's most elegant and impressive resorts, the Inn at Perry Cabin (308 Watkins La., 410-745-2200), a sprawling colonial-style hotel on the north edge of town, overlooking the water. A member of the swanky Orient-Express Hotels group, the inn is built around what had been a country manor constructed nearly 200 years ago. Having expanded considerably since it became an inn in 1990, the 25-acre property has 81 rooms and suites, each decorated individually and most with water views - many have fireplaces, deep soaking tubs, and private balconies. There's a fine restaurant serving three meals daily, plus high tea in the afternoon (enjoy it on the terrace when the weather permits), and a richly nautical bar called Purser's Pub. Other amenities at this regal getaways include a pool, fitness center, docking facilities, lovely gardens, and the serene, full-service Linden Spa, which offers a full and impressive range of treatments. For a special occasion, or if planning a same-sex wedding, this beautiful property is a memorable choice.

In downtown St. Michaels, an easy walk from shops and restaurants, the rambling and historic Old Brick Inn (401 S. Talbot St., 410-745-3323) is another appealing and romantic option. Comprising three adjacent, carefully restored buildings containing a total of 20 rooms, this charming property is done with rather lavish colonial furnishings - many rooms have exposed-brick walls, four-poster beds, Jacuzzi tubs, and separate sitting areas. The inn is just a couple of blocks from the water. Situated right on the harbor, across a quaint pedestrian bridge from the Maritime Museum, the eight-room Hambleton Inn B&B (202 Cherry St., 410-745-3350) is another stunner, with Oriental rugs, hardwood floors, well-equipped private bathrooms, and individual climate control in the rooms; rates include an impressive full breakfast.

Among area restaurants, Bistro St. Michaels (403 S. Talbot St., 410-745-9111), which is beside the Old Brick Inn, is an exceptional choice for dinner and weekend brunch; the kitchen focuses on locally sourced ingredients in such tasty creations as sautéed chicken livers over citrus salad with bacon lardons, feta, and local honey; and a honey-and-mustard braise of rabbit leg, pork spareribs, and spicy sausage with thyme wild rice. Nearby Ava's Pizzeria & Wine Bar (409 S. Talbot St., 410-745-3081) is another good bet; grab a seat on the patio on warm days.

Speaking of vino, just up the street is St. Michaels Winery (609 S. Talbot St., 410-745-0808), which has a tasting room with copper-top tasting tables, and crafts pretty respectable dry whites and reds as well as some sweeter wines. There's a cute, informal restaurant next door called Gina's Cafe (601 S. Talbot St., 410-745-6400) that turns out inexpensive and filling Mexican food, including delicious crab-topped nachos. For dining on the water, look to the classic Crab Claw Restaurant (304 Burns St., 410-745-2900), a traditional favorite for hearty lunches and dinners of fresh local seafood: oysters casino, lump crabmeat cocktail, fried flounder sandwiches, rockfish and chips, fried soft-shell crabs, and the like. It's adjacent to the maritime museum. Finally, for a perfect sweet treat on a warm summer day, drop by Justine's (106 Talbot St., 410-745-0404) for a scoop (or several) of old-fashioned, homemade ice cream. You'll encounter a fun, friendly staff and ice cream in more than 20 flavors.

For tourism information on St. Michaels, visit the website of the St. Michaels Business Association (800-808-7622).

Was this page helpful?