Plan a Winter Vacation by the Bay

Courtesy of Tidewater House

In the laid-back yet sophisticated towns along Maryland’s Eastern Shore, the season is filled with opportunities to indulge multiple passions (in a socially distanced fashion).

Where to Stay

The Inn at Perry Cabin has been a landmark in St. Michaels since just after the War of 1812. The ambiance is a mixture of contemporary design and Old World class and service. Guest can end the day by the fireplace in one of the deluxe guestrooms or with cider and s’mores at the fire pit. Complimentary bikes are available for anyone interested in a bracing excursion taking in the scenery and exploring downtown St. Michaels. Starting at $579. 308 Watkins Lane, St. Michaels, (800) 219-2374, innatperrycabin.com.

In downtown Easton, the Tidewater House (formerly the Inn at 202 Dover) is open weekends in winter. The gracious 1874 mansion offers five guest quarters, four suites and one room, each tastefully furnished with antiques and antique reproductions to reflect exotic themes ranging from Asian to African safari. You’ll be welcomed with a bottle of wine or champagne and French macarons. $239-$329. Check-in at Tidewater Inn, 101 E. Dover St., Easton, (410) 822-1300, tidewaterinn.com.

Open weekends in winter, the newly remodeled Tilghman Island Inn provides upscale, comfortable lodging with gorgeous views of the Chesapeake Bay and the Eastern Shore sunsets. $225-$260. 21384 Coopertown Road, Tilghman Island, (410) 886-1170, tilghmanislandinn.com. 

Named for the local heroine who saved the brick building from burning by the British during the War of 1812, the Kitty Knight House offers charming accommodations at a moderate price. Ask for a room overlooking the Sassafras River. $150-$235. 14028 Augustine Herman Hwy., Georgetown, (410) 648-5200, kittyknight.com.

Where to Eat

Tis the season when local watermen are hauling in oysters by the boatload. Eat your fill of them—on the half shell or in a po’ boy sandwich—at Tickler’s Crab Shack & Restaurant, where the seafood is delivered daily fresh from the docks. $14-$42. 21551 Chesapeake House Drive, Tilghman Island, (410) 886-2121, wylderhotels.com.

Get a real taste of Eastern Shore ingredients on the three-course prix fixe menu created by chef Gregory James at Stars. The fall menu included Chesapeake crab soup, tenderloin au poivre, and Chesapeake Bay flounder with maitake mushroom ravioli. A separate prix fixe vegetarian menu is also available. $75-$95 per person. Inn at Perry Cabin, 308 Watkins Lane, St. Michaels, (800) 219-2374, innatperrycabin.com.

Breakfast and brunch are special occasions at Hunters’ Tavern, where you can enjoy your crab in a Benedict or an omelet. For brunch, start with snapping turtle, cream of crab or Maryland crab soup, or Eastern Shore crab and artichoke dip. For your main course, try the fried oyster platter $11-$20. Tidewater Inn, 101 E. Dover St., Easton, (410) 822-1300, tidewaterinn.com.

The stone-hearth oven-baked pizza at Out of the Fire is superb. Try the duck sausage or the white pie with fresh mozzarella, ricotta and roasted garlic. Delectable main courses include shrimp and grits, and seared sea scallops with coconut milk, braised cabbage and cashews. $16-$32. 22 Goldsborough St., Easton, (410) 770-4777, outofthefire.com.

208 Talbot will tempt you with contemporary twists on traditional favorites. Highlights include the short rib pierogis, lobster spring rolls, seafood pappardelle and miso-glazed duck breast. $23-$36. 208 Talbot St., St. Michaels, (410) 745-3838, 208talbot.com.

Outdoor (& Indoor) Fun

Weather permitting, you can play a round on the Links at Perry Cabin, a championship 18-hole golf course and the last designed by the legendary Pete Dye. You can also practice on a high-definition golf simulator, where can choose top courses from Pebble Beach to the Old Course at St. Andrews. $72-$117 weekdays, $84-$142 weekends; includes cart. 

Eastern Neck National Wildlife Refuge is a winter home for thousands of waterfowl, including the majestic tundra swans and bald eagles building nests and laying eggs. Free. 1730 Eastern Neck Road, Rock Hall, (410) 639-7056, fws.gov.

Osprey and bald eagles also inhabit the 53-acre Black Walnut Point Natural Resources Management Area at the southern tip of Tilghman Island. (410) 820-1668, dnrmaryland.gov.

Indulge in a treatment or package at the Terrasse Spa at Talbot House, where you can share a side-by-side couples massage or an 80-minute package that includes a hydrating body polish, peppermint foot treatment and scalp and body massage. At the Spa at the Inn at Perry Cabin, try an 80-minute full-body massage and pampering foot treatment with sparkling wine service, or a wrap and massage with coconut milk. $225-$440.

In February and March, world-class chef Mark Salter offers intimate Saturday- morning cooking demos at his Robert Morris Inn in Oxford. The event includes a lovely two-course lunch with a glass of wine and recipes to take home. $85-$90 per person. 314 N. Morris St., Oxford, (410) 226-5111, robertmorrisinn.com.

Take a spin on the ice indoors at the Talbot County Community Center. Admission $7, skate rental $3. 10208 Ocean Gateway, Easton, (410) 770-8050, talbotparks.org.

Arts, Antiques & More

In Easton, you’ll find an eclectic selection at Easton Antiques & Art Gallery (25 N. Harrison St., Suite A, 410-763-9298) and Foxwell’s Antiques & Collectibles (7793 Ocean Gateway, 410-820-9705). Oxford is home to Americana Antiques, with an interesting mix of carousel figure and folk art, furniture, and period accessories. (111 S. Morris St., Oxford, 443-786-4486, americanaantiques.net). And for nautical collectibles, sterling silver, coins, jewelry, furniture and stained-glass windows, head for St. Michaels and Antiques on Talbot (211 N. Talbot St., 410-475-5208, antiquesontalbot.com).

If you’re in Easton and looking to add to your personal art collection, the Trippe Gallery features landscape, figurative and impressionist works in oils, pastels and watercolors (23 N. Harrison St., 410-310-8727, thetrippegallery.com). Paintings and sculptures are on display at Studio B Gallery (7B Goldsborough St., 443-988-1818, studiobartgallery.com). Troika Gallery specializes in fine paintings and portraits (9 S. Harrison St., 410-770-9190, troikagallery.com).

St. Michaels’ petite Talbot Street shopping district will have you browsing for hours. Guilford and Company offers a spectacular collection of antique and estate jewelry. 101 N. Talbot St. (410) 745-5544, guilfordandcompany.com. At the Gatz Home & Garden, you’ll find a fascinating selection of stained-glass doors and windows, European antique furnishings, marble fireplace mantels, fountains, and gazebos. 1210 S. Talbot St., (410) 745-3700, thegatz.com. For one-of-a-kind handmade home furnishings and accessories, visit 1.O.A.K.  202 B South Talbot St., (410) 745-8032. And to weather the winter, wrap yourself in a cozy cashmere cardigan or duster from Chesapeake Bay Outfitters. 114 S. Talbot St., (410) 745-3107, cbostyle.com.

For History Lovers

In addition to its extensive permanent collection of American and European drawings, photographs and prints, the Academy Art Museum hosts seasonal national and regional exhibitions. $3. 106 South St., Easton, (410) 822-2787, academyartmuseum.org.

The Eastern Shore’s nautical past and present is celebrated at the 18-acre indoor/outdoor Chesapeake Bay Maritime Museum. Tour a waterman’s shanty, talk with a shipwright or visiting captain, see shipwrights building and restoring traditional watercraft, explore the fleet of eight docked restored vessels, and take in the panoramic harbor and river views from the top of the 1879 Hooper Strait Lighthouse. $14. 213 N. Talbot St., St. Michaels, (410) 745-2916, cbmm.org. 

Relive aviation’s early days at Massey Air Museum, where you can tour two hangars filled with vintage aircraft, artifacts and hands-on exhibits. Most days, you can also see planes being restored at the shop. If the hangar doors are closed, just ask someone or call. They’ll open up for you. Free. 33541 Maryland Line Road, Massey, (410) 928-5270, masseyaero.org. 

Beer, Wine and Spirits 

If local brews are your preference, visit Eastern Shore Brewing for a five-sample flight to go. For a bold choice, try the seasonal Duck Duck Goose Porter. 605 S. Talbot St., St. Michaels, (410) 745-8010, easternshorebrewing.com.

At St. Michaels Winery, you can savor a no-contact nine-sample tasting box of their merlot, vidal blanc, pinot gris and more. For a superb dessert wine, try the Chocolate Zin. 609 S. Talbot St., St. Michaels, (410) 745-0808, st-michaels-winery.com.

Even if the tasting rooms are closed due to COVID-19 restrictions, you can still sample the distinctive spirits at Lyon Rum Distillery. It’s easy to arrange for curbside delivery of their delightfully different rum and rum liqueurs in flavors like blackberry, Curacao orange, coffee, pineapple and coconut. 605 S. Talbot St., Unit 6, St. Michaels, (443) 333-9181, lyondistilling.com.

NOTE: With changing restrictions on hospitality venues and recreational activities due to COVID-19, call ahead or go online before making travel plans.