Waterfront Vineyards and Chocolate Wine

The Eastern Shore hasn’t been known for wines, but a few ambitious vineyards are hoping to change that.

Start at St. Michaels Winery, housed in a historic flour mill in the heart of St. Michaels. It opened three years ago and has wasted no time in gaining a following thanks to such innovative concoctions as “Chocolate Zin.” Many of the wines pay homage to the Chesapeake Bay—for example, “Gollywobbler,” a Concord/Cabernet blend named for a type of log-canoe sail. Tastings cost $6 to $15, although there’s a $1 one-sample deal for designated drivers. 605 S. Talbot St., Unit 6, St. Michaels; 410-745-0808; st-michaels-winery.com. Monday through Friday noon to 6, Saturday noon to 7, Sunday noon to 4.

A few doors down is Market House, a hip one-stop shop for affordable gourmet food. Owner Jen Bridges will pack a picnic with imported cheeses, soft-shell crabs, and a baguette with house-made wine butter that you can take to nearby Muskrat Park to eat by the water. 415 S. Talbot St., St. Michaels; 410-745-6626; markethousegourmet.com. Monday through Thursday 8:30 to 6, Friday and Saturday 8:30 to 7:30, Sunday 8:30 to 6.

Next, head about ten miles to Little Ashby Vineyards in Easton. This boutique winery was the first one licensed on the shore, and the Bordeaux blend called “Super Talbot” has won many awards. Little Ashby delivers the quintessential Eastern Shore experience: It’s along the banks of the Miles River, where herons, ospreys, and other waterfowl frolic. Tours and tastings are by appointment, but because owners Lynne and Warren Rich live on the property, they welcome the public warmly, even for last-minute visits. 27549 Ashby Dr., Easton; 410-819-8850; littleashbyvineyards.com.

Experience a different side of the Eastern Shore by driving to Tilmon’s Island Winery, one of the smallest in Maryland. The vineyard is in the farming community of Sudlersville, and the drive weaves and bobs past pretty corn and soy farms. The winery is about 35 miles from Easton but worth the trip. Owner Don Tilmon is an agricultural economist, and his straightforward Merlot and Cab Franc are fine testaments to his study. Free tastings are offered on the deck of the Tilmons’ home, overlooking a pasture and the small Concord-grape vineyard that produces their most popular sweet wine, “Judy’s Red Hat Red.” 755 Millington Rd., Sudlersville; 443-480-5021; tilmonswine.com. Saturday noon to 5; by appointment other days.

Staying for dinner? Try Restaurant Local in Easton. Groups as small as four people and as large as 16 can dine in the private Decanter Wine Room, where Dick Cheney and Oliver North have been spotted. The glass-enclosed boîte flanked by walls of wine is the perfect ending to a winetasting day. Couples should head outdoors to the patio, where they can dine beside a stone fireplace. 101 E. Dover St., Easton; 410-819-8088; restaurantlocal.com. Entrées $23 to $49.

Planning to stay the night? Consider the Inn at Perry Cabin in St. Michaels, where you’ll feel as though you’re visiting a wealthy aunt’s waterfront estate. Rooms in the historic section are chintz-and-antique-filled, while those in the new wing feature a nautical theme and marble bathrooms. Before bed, tuck into the cozy Purser’s Pub and enjoy a glass of wine in front of the fire. 308 Watkins La., St. Michaels; 410-745-2200; perrycabin.com. From $330.

For more information about area wineries, including maps and upcoming festivals, go to marylandwine.com and virginiawines.org.

This article first appeared in the September 2008 issue of The Washingtonian. For more articles from that issue, click here