St. Michaels & Easton, MD

Though both are a bit further of a drive than Annapolis (a drive that requires a pass over the Bay Bridge, no less), I much prefer these two enclaves when it comes to exploring the Eastern Shore. St Michael’s can feel a bit nautical and Easton feels a bit more refined, but both have a lovely, relaxed temperament and some great little shops. It takes about 20 minutes to drive between them, and you’ll drive through one on the way to the other. Each time I’ve visited this area, I’ve stayed for a night at the Wildset – dinner at Ruse always, always tempts me. You can definitely make it to Easton and back in a day, but why rush a good thing?

My favorite memories

Each stay I’ve had at The Wildset, as well as every dinner I’ve enjoyed at the hotel restaurant Ruse. This place along is worth the trip!

The Modern Bulldog, perhaps one of my favorite stores in the entire DMV.

Strolling the main street of St Michaels, and wandering in and out of the cute neighborhood on the East side of main street – some of these homes back straight up to the water, and it’s so charming.

Getting a sweet treat at Bonheur in Easton, and I also had a good coffee from Weather Gage around the corner.

Some great antique finds at Antiques on Talbot in St Michaels.

Enjoying a leisurely lunch at Inn at Perry Cabin, especially in the early summertime.

Recommendation:
The Wildset Hotel

I adore this hotel – I think I’ve stayed two or three times at this point. The rooms are minimal but comfortable, and the fireplace is such a fun touch in the fall and winter. It’s right on the main street in St Michaels, so it’s an easy home base for exploring. What really makes the hotel special though is the restaurant, Ruse – every meal here has been one of my favorites in the area. Maybe it’s being just a couple of hours away from DC, cared for by people who aren’t in as much of a hurry, but I think the restaurant is worth a visit alone. Also, the hotel’s reception area is a cute little shop with finds I wish I could source more easily in DC!

Recommendation:
The Modern Bulldog

Ask me what shop surprised me the most in all of the DMV, and I’d answer The Modern Bulldog. I stumbled upon this place in downtown Easton while out and about with a few friends, and I told them to go on without me – I needed a moment to take in what heaven would feel like. It was a fever dream. This shop specializes sourcing and restoring gorgeous mid century modern furniture, assembled in a crisp, collected fashion. It’s perfect in every way.

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Frederick, MD