Part 13 of our 25-part Southeast road trip series takes us to the Free State — and Maryland is one of the most surprisingly dog-friendly and geographically diverse states in the entire country. From the wild shores of Assateague Island and the charming colonial streets of Annapolis to the craft beer scene of Baltimore and the rolling mountains of Western Maryland, the Old Line State packs an extraordinary amount of variety into a relatively small footprint.
🐾 Why Maryland?
Maryland is often overlooked as a road trip destination, but it absolutely shouldn't be. The Chesapeake Bay defines the state's character — its seafood, its culture, its landscape — and it's one of the most beautiful bodies of water in America. Annapolis is one of the most charming small cities on the East Coast. Baltimore has reinvented itself as a food and craft beer destination. And the Eastern Shore offers a laid-back, dog-friendly coastal experience that rivals anything in the Southeast. Dogs are welcome throughout, and Maryland's compact size makes it easy to experience a lot in a short time.
🏨 Pet-Friendly Hotels & Stays
Kimpton Hotel Monaco — Baltimore
Kimpton's Baltimore property brings their signature zero-pet-fee policy to a stunning historic building in the heart of downtown. Steps from the Inner Harbor, Fells Point, and some of Baltimore's best restaurants, it's a perfect dog-friendly base for exploring Charm City.
Annapolis Waterfront Hotel — Annapolis
A beautiful waterfront hotel in the heart of Annapolis that welcomes pets. Steps from the City Dock, the Naval Academy, and the charming streets of downtown Annapolis, it's one of the most scenic dog-friendly hotel locations on the entire East Coast.
Refuge Hotel — Chincoteague (VA side) / Ocean City area
For those exploring the Eastern Shore and Assateague Island, several pet-friendly properties near Ocean City and the Delaware border make great bases for coastal exploration with your dog.
The Inn at Antietam — Sharpsburg
A beautiful historic B&B near the Antietam National Battlefield in Western Maryland that welcomes dogs. A peaceful, atmospheric stay in one of America's most historically significant landscapes.
Deep Creek Lake Vacation Rentals — McHenry
The Deep Creek Lake area in Western Maryland has dozens of pet-friendly vacation rental cabins and cottages. A perfect base for exploring Garrett County's mountains, state parks, and the lake itself with your pup.
🍽️ Pet-Friendly Restaurants & Cafés
LP Steamers — Baltimore (Locust Point)
A beloved Baltimore institution with outdoor picnic tables where dogs are welcome. Steamed blue crabs, cold Natty Boh, and a waterfront setting — this is the quintessential Maryland crab experience, and your pup is invited.
Boatyard Bar & Grill — Annapolis
A classic Annapolis waterfront restaurant with a large dog-friendly outdoor deck overlooking Back Creek. Fresh Chesapeake seafood, cold drinks, and a lively sailing crowd make this one of the best patios in the state.
The Narrows — Grasonville (Kent Island)
A beautiful waterfront restaurant on Kent Island with a dog-friendly outdoor area overlooking the Chester River. Fresh local seafood, stunning water views, and a warm Eastern Shore atmosphere — a perfect stop on the way to or from the beach.
Dogfish Head Alehouse — Gaithersburg & Fairfax
The beloved Delaware craft brewery's Maryland outpost has a dog-friendly outdoor area. Great craft beer, solid pub food, and a welcoming atmosphere in the DC suburbs.
Brewer's Art — Baltimore (Mt. Vernon)
A celebrated Baltimore restaurant and brewery in a stunning historic mansion with a dog-friendly outdoor area. One of Baltimore's most beloved institutions, with exceptional Belgian-inspired beers and creative American cuisine.
🍺 Dog-Friendly Breweries
Heavy Seas Beer — Baltimore
One of Maryland's most celebrated craft breweries with a large dog-friendly outdoor space. Their Loose Cannon IPA is a Maryland classic, and the taproom has a great nautical atmosphere that captures the spirit of the Chesapeake.
Checkerspot Brewing Company — Baltimore
A Baltimore craft brewery with a dog-friendly taproom and outdoor space. Creative small-batch releases and a welcoming atmosphere in one of Baltimore's most vibrant neighborhoods.
RAR Brewing — Cambridge (Eastern Shore)
A beloved Eastern Shore craft brewery in the charming town of Cambridge with a dog-friendly outdoor space. Their Nanticoke Nectar IPA is a local favorite, and the taproom has a great community feel that captures the laid-back spirit of the Eastern Shore.
Smoketown Brewing Station — Frederick
A Frederick craft brewery with a dog-friendly outdoor space in one of Maryland's most charming small cities. A great stop on the way to or from Western Maryland, with a rotating tap list and a welcoming atmosphere.
Garrett County Brewing — McHenry (Deep Creek Lake)
A craft brewery in the Deep Creek Lake area with a dog-friendly taproom and patio. A perfect post-hike stop after a day in the Garrett County mountains, with local beers and a relaxed mountain atmosphere.
🌲 Dog-Friendly Parks & Trails
Assateague Island National Seashore — Berlin
One of the most magical natural areas on the entire East Coast, Assateague Island is home to wild ponies and miles of pristine Atlantic beach. Leashed dogs are welcome on the beach and trails year-round — one of the few East Coast national seashores that welcomes dogs on the beach. Don't miss it.
Catoctin Mountain Park — Thurmont
A beautiful national park in the Blue Ridge foothills of Western Maryland with dog-friendly trails through hardwood forest. Camp David is located within the park, adding a layer of historical intrigue to an already lovely hiking destination.
Patapsco Valley State Park — Ellicott City
A stunning linear state park along the Patapsco River just west of Baltimore with dog-friendly trails, swimming holes, and historic railroad bridges. One of the best urban outdoor escapes in the entire Mid-Atlantic.
Seneca Creek State Park — Gaithersburg
A beautiful state park in the DC suburbs with dog-friendly trails along Seneca Creek and around Clopper Lake. A great green escape for dogs visiting the Washington area.
Swallow Falls State Park — Oakland (Western Maryland)
A stunning state park in Garrett County with dog-friendly trails past a series of beautiful waterfalls, including Muddy Creek Falls — the tallest free-falling waterfall in Maryland. One of the most beautiful short hikes in the entire state.
Sandy Point State Park — Annapolis
A beautiful state park on the Chesapeake Bay near Annapolis with dog-friendly beach access and stunning views of the Bay Bridge. A perfect afternoon stop for dogs who love the water.
🗺️ Suggested Road Trip Route
Start in Baltimore (Fells Point + LP Steamers + Heavy Seas) → south to Annapolis (City Dock + Boatyard Bar) → east across the Bay Bridge to the Eastern Shore (Kent Island + Cambridge + RAR Brewing) → south to Assateague Island (wild ponies + beach) → OR west from Baltimore to Frederick & Western Maryland (Catoctin + Deep Creek Lake + Swallow Falls).
Maryland is compact enough to do both loops in a single week-long trip.
🐶 Pro Tips for Maryland Road Trips
- Assateague's wild ponies are beautiful but can be aggressive — keep dogs on leash and maintain a safe distance from the ponies at all times.
- Blue crab season peaks in late summer (August-September) — the best time to visit for the full Maryland seafood experience.
- Annapolis gets extremely crowded during the US Naval Academy graduation in May — plan around it or embrace the pageantry.
- The Eastern Shore is best explored at a slow pace — take the back roads and stop in small towns like St. Michaels, Oxford, and Easton.
- Deep Creek Lake is a year-round destination — beautiful in fall foliage season and a great ski/snowshoe destination in winter for adventurous dogs.
Up Next in the Series
Stay tuned for Part 14: Delaware — where we'll explore the dog-friendly beaches of Rehoboth, the charming streets of Lewes, and the wild shores of Cape Henlopen. Subscribe to our newsletter so you never miss a stop!
Have a favorite dog-friendly spot in Maryland we should add? Drop it in the comments!