Road Trip: Talbot County MD


In our April issue of Martha Stewart Living, we featured this lovely area on the Eastern Shore of Maryland. It’s long been a weekend destination for Baltimore and D.C. natives, but it’s only four hours from New York!  The main little towns we focused on are Easton, St. Michaels, and Oxford, all within a short drive of each other.

Where to Stay:

Inn at Perry Cabin: It’s a hotel you’d want to go to, even if it was in the middle of nowhere—great restaurant, inspired gardens, and lovely water views. And the décor is great—cozy, comfy, elegant. Fresh flowers everywhere—in the rooms, public spaces…cozy public spaces with lovely furniture. Kayaks available for checking out the Miles River, and bikes to go into town.  Cookies made and put in the room every night, cooked by Mrs. Gussy, who has been making them for 24 years. It’s about a 5-10 minute walk into St. Michaels town.

Dr. Dodson House: Right in the middle of St. Michaels, and it’s a real favorite that locals recommend—5 star accommodations, and historic details abound.

Sandaway B&B: A waterfront property in Oxford, that actually has a sandy beach! Although we did not stay here, it looks to be a lovely property and not as expensive as some of the other options.

Where to Eat:
The Crab Claw: Whether you commit to the blue crab extravaganza (you should) of crabs cooked in Old Bay Seasoning, award-winning crabcakes, or buckets of steamed clams…you just have to come here. It’s been around since 1965, same family, and it’s awesome. In warm weather, sit outside on picnic benches, looking out onto the Miles River, and while you wait, feed the ducks some corn. Try the cheese and pickles starter platter for $5.95. It’s so good. Watch families gather together and order piles, and piles, and piles of crabs.

Sherwood Landing:
Go for dinner at the Inn at Perry Cabin, and tuck into a fancy, but worth it dinner. Every purveyor is listed, and the wine list is extensive. But don’t worry, the waiters are opinionated, and smart, but not overbearing. The crab cakes were epic, as was the Smith Island cake.

Key Lime Café: A good breakfast spot in St. Michaels—go for the scrambled eggs with lump crab, and even if it seems decadent, don’t miss the homemade key lime pie.

Robert Morris Inn: In sleepy historical Oxford, this is the spot to get lunch. From local oysters to burgers, this British chef gets it right.

Afterwards, take a walk to the Scottish Highland Creamery, and splurge on an ice cream—they’re all homemade, with great flavors like coffee chocolate crunch, and pooh bear honeycomb ice cream.

What to Do:

In St. Michaels, a walk down main street (S. Talbot St.) which is filled with shops—our favorites—the estate jewelry shop Guilford & Company, the classic toy store Calico Toys & Games, and Big Al’s, to pick up some lump crab to bring home. If you’re not staying at the Inn at Perry Cabin, you should definitely check out their beautiful gardens, and don’t forget your camera.

Chesapeake Maritime Museum: It’s such a great museum it’s really worth building a trip around, even if you didn’t think you were into boating. Learn about the oyster and crab industries, and…build in some time to take a historic boat cruise on the Patriot. You can even be a drop-in boat-building apprentice for a day!

Easton: Walk around the historical downtown and meander into the Garden and Historical Society—we loved the herb garden with it’s okra and purple beans. Shop at the Easton Antiques and Art Gallery, which has a mix of great finds—like a beaver top-hat in it’s original case for $150, an English car picnic basket, and and Danish credenza. The Hills Pharmacy may look like any old-school drugstore, but walk through to the back, and there’s a tin-ceilinged soda shop. We did not make it to the Amish County Farmer’s Market, but it came highly recommended.

Oxford: Walk down the main street and check out all the historical homes, and the little Oxford Museum. Pick up some cards by John Moll there, and also look at the boat builders Cutts&Case.

Oxford-Bellevue Ferry:
It’s the oldest continuous running ferry in the country—since 1683, and it runs every 15-20 minutes.

Comments (12)

  • As a Talbot County native ( and a journalist) I skimmed and found two errors! Fact check “Aven River” at the Crab Claw and I assure you, Chance hasn’t worked anywhere close to 19 years at Perry Cabin!

  • Love the blog – Talbot County is a great destination. I would like to point out to your readers that Easton Antiques and Art Gallery is also the home of Shore Boys Soups – they make it in a commercial kitchen in the back of the store and sell it frozen by the pint. Their Cream of Crab Soup is worth the trip!

  • Perry Cabin sits on the Miles River not the Aven….Oxford sits on the Tree Avon River.

  • I agree, worth the trip from nyc We spent a wonderful week in the area .
    The Crab Claw is the place to go

  • we chartered a boat from Annapolis at letsgocruising(.com) and spent a lovely three days exploring St. Michael’s. With a view of the Inn at P.C. and overlooking the maritime museum, it was so charming! Definitely can’t miss it, and I do recommend seeing the chesapeake from the water if you get a chance!

  • I was tickled to see this feature when I opened the new issue over the weekend! We discovered that staying in St. Michaels is the perfect way to break up the long drive from Maine to North Carolina that we so often make to visit our families. Not only do we love staying at the Inn at Perry Cabin, but our dog loves it too! We look forward to checking out the rest of Talbot County on our next trip!

  • Thank you for including Dr. Dodson House B&B! We love St. Michaels – this is our 20th season and St. Michaels gets better each passing year – always something new coming to town. This year watch for Lyon Distilling Co. – a craft distillery at The Old Mill. Be sure to eat at Ava’s and Theo’s, our two favorites.

  • lLiving outside of DC the drive to the Eastern Shore is even a day trip! And we love visiting Oxford and The Scottish Highland Creamery for homemade candies and Ice Cream but you missed a great photo-op with the owner, a true transplanted Scotsman, Victor Barlow serving you in his kilt!

  • Thank you for including Key Lime Cafe in your article.
    Located in what once was the John Miles House in the historic district of St.Michaels, Key Lime Cafe has been serving folks from all over for 9 years – breakfast, lunch, and dinner. Come to the beautiful Eastern Shore of MD for good fun, and food!

  • Thank you for your kind words about Sandaway B&B and Oxford, Maryland. You are invited to stay with us next time :)

  • I love the great state of MD. I recently married a Chesapeake Bay gentleman and I am very pleased with all areas of MD. We married in St Michaels aboard the Selina ll with Captain Iris Clark officiating the nuptials. We honeymooned on the beach at Asateague Island. We’ve traveled to the upper Bay Area of HaveDGrace, Chestertown.
    This blog reminds me of all the areas I love and want to be. Thank you for the beautiful pictures and restoring my hopes of living somewhere on the Chesapeake Bay in MD.
    We now reside in KY and hope to relocate sometime soon.

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