We’re continually on the hunt for experiences that add richness to our lives. In the spirit of the revival of road trips, we are proud to begin a regular, monthly section to feature destinations within driving distance of Charleston. We feel that our smart and savvy readers will find these trips enriching and entertaining.


Talbot County, Maryland

Driving a little over six hours East of Charleston brings you to Talbot County, Maryland. I realize this is a bit further than destinations we usually feature, but I promise it’s worth the extra time. Talbot County is comprised of four towns: Easton, St. Michaels, Oxford, and Tilghman Island. It is part of the Chesapeake Bay region with many miles of photogenic shoreline. While Tilghman Island offers impeccable scenery (and sometimes eagles!) and Oxford, a small waterside town with under 1000 people, has lovely Victorian architecture, the majority of things to do are in Easton and St. Michaels.

Where to Stay in Talbot County

Easton, the first town you will come to, is home to the Tidewater Inn, a gorgeous red-brick luxury bed-and-breakfast. Ninety-two modern boutique rooms are available plus a fantastic on-site restaurant. It is also within walking distance to many boutiques, coffee shops, and art galleries. Those wishing to save a few bucks will be shocked by the Best Western Plus Easton Inn and Suites. It is under $100 a night and the swankiest BW property I’ve ever seen.

If you are looking to splurge, opt for the Inn at Perry Cabin in St. Michaels, a colonial mansion that was used in the movie “Wedding Crashers”. The inn has a world-class spa, stellar dining facilities, beautiful terrace, stunning manicured grounds, plus a daily afternoon tea complete with scones, gourmet breads, and tea. Relaxing in the yacht-lined waterfront Adirondack chairs at sunset is magnificent.

Where to Dine in Talbot County

Grab a quick lunch at Krave Courtyard where the Toasted Walnut Chicken Salad (with grapes and green onions) and Tuna Salad are exceptional. A second choice would be Hunter’s Tavern, a classy restaurant at the Tidewater Inn with a great patio. Both the Deep Dish Quiche and Eastern Shore Crab Roll are lip-smacking good.

Awful Arthur’s Seafood Company, which makes the best-blackened tuna bites (with wasabi cream sauce), is perfect for lunch or dinner. Foxy’s Harbor Grille offers outdoor riverfront dining with a plethora of craft beers and amazing Ahi Poke. A romantic eatery, Scossa Restaurant, has toothsome Potato Gnocchi with Veal Ragu and Spinach & Ricotta Ravioli with butter and sage sauce.

St. Michaels and Easton are 17 minutes apart so there is not much driving between distances.

What to Do on Your Weekend Trip

You will have the best crab of your life in Talbot County, so crabbing would be a fun thing to try if you haven’t already. Other outdoor activities include kayaking, canoeing, sailing, and taking a yacht cruise.

Both Easton and St. Michaels are big in the art scene so galleries are plentiful and worthwhile. A few of my favorites are Grafton Gallery, Dragonfly Galleria, and Academy Art Museum. Shoppers are going to rejoice in the selection of small boutiques with unique items. Recommended shops are The Christmas Shop, Chef and Shower, Bountiful Interiors, and Olivins Tasting Room for the best olive oils and vinegar ever!

You will find two top-notch food tours in Talbot County: Eating St Michaels and Eating Easton. A small group of people are taken to four or more local eateries and introduced to restaurant owners and chefs for an up close and personal experience lasting three hours. The tour guide shares local lore and historical facts about the beautiful town along the way. Tours only run on the weekend during the off-season.

Since you are on the Eastern seaboard, you must visit the Hooper Strait Lighthouse, built in 1879. Also, stop by the Chesapeake Bay Maritime Museum, the #1 rated attraction in the area. It includes 18 waterfront acres with hands-on activities and exhibits. Guided tours from 90 minutes to four hours are available as well as boat rides.

If wineries are of interest, visit Triple Creek Winery in Cordova, Maryland, 15 minutes from Easton. The tasting room is darling and the wines are fine. Lyon Distilling Company is another adult stop for tasting small batch spirits including rum, vodka, and gin.

Talbot County is rich in history, so visiting the Wye Grist Mill, the oldest continually operating grist mill in the country (325+ years!), is necessary. Wye, a historic landmark, provided flour to feed George Washington’s troops at Valley Forge.

Talbot County, Maryland: A Place Worth Seeing

Stunning scenery, the freshest seafood, and interesting culture make up Talbot County, Maryland. I was blown away by the coastal views and terrific sunsets. It truly made me feel relaxed like no other place; a large-scale coastal seaside Dicken’s village of sorts. Make this a road-trip priority before the rest of the country discovers how marvelous it is. The charm and laid-back feel will instantly win you over.