If you’re looking for a quick, dog-friendly weekend getaway with the pup outside of DC, Maryland’s Eastern Shore is great! It’s close enough that you don’t have to think about it *too* much, and far enough that it feels like a little escape from the norm.

We didn’t do a ton of research ahead of time, which is a pretty risky move when traveling with Benson, but we heard great things about the dog-friendliness of this area.

Here’s what we did (so you don’t have to research too much, either)!

Annapolis, MD

We started in Annapolis, MD, which surprisingly has quite a few restaurants with patio spaces that do NOT allow dogs (we got turned away by 2 patio restaurants before we discovered our final landing spot, so if you’re going to stray from this itinerary, definitely call ahead first).

1. Sea Dog Pet Boutique: on our search for dog-friendly lunch spots near the water, we stumbled into the Sea Dog Pet Boutique, which was adorable. They gave Benson a treat and lots of love, along with some recommendations for where we can explore in the area.
2. Federal House Bar & Grille: The Federal House has a huge outdoor patio area and they welcome dogs with open arms – they have water bowls positioned at every outdoor table, and they also have an adorable doggy food menu!

St. Michaels, MD

After lunch, we drove another hour to St. Michaels where we spent the rest of the afternoon exploring the town. St. Michaels is SUPER dog-friendly, and a lot of places actually allow leashed dogs inside and outside.

1. Foxy’s Harbor Grill: We wanted to sit outside near the water for a drink, and we stumbled upon Foxy’s Harbor Grill. It has a super cute patio space and covered bar area, with delicious “crushes” of all different flavors (I had the King’s Crush, and it did not disappoint).
2. Bordeleau Winery: This winery is positioned on the main street, and it allows dogs inside and out! The owners LOVED meeting Benson and they even greeted us with a treat at the door when we walked in.
3. Blue Heron Coffee: Cute local coffee shop. A few outdoor tables and chairs. Definitely order an oat milk lavender latte, and you won’t regret it.
4. Boat Tours and Water Taxi: We didn’t get a chance to do this, but St. Michaels boat tours are pet friendly! And they even do an evening booze cruise, so we’ll be back to check this out next time!

Tilghman Island, MD

Wylder Hotel Tilghman Island: we stayed overnight about 20 minutes outside of St. Michaels on Tilghman Island. This hotel is pet-friendly with an indoor and outdoor onsite restaurant. There are tons of water activities like canoes and kayaks, a few lawn games, and spectacular views of the water. They will charge a pet fee for cleaning, so just call ahead to confirm the cost of that fee!

Have you been to the Eastern Shore with your pup? Tell us your favorite places to go, and we’ll check them out next time!