Amazing shore weekend getaways from Philadelphia, Baltimore or Washington DC

A great American getaway in pieces, we journey from the urban hubs of either Philadelphia, Baltimore or Washington DC towards maritime outposts on the eastern shores. Begin your weekend getaway diving into the diversity of Baltimore’s Charm City or discovering how Philly became a forerunner in the gay rights movement, before moving closer to shore where slower, saltier ways of life await. Regardless of the jumping-off point, you’ll soon need your flip flops and your chapstick to enjoy the region’s best shore-side state parks, sheltered beaches and all of the seafood your heart desires. Discover the best weekend getaways from DC, Baltimore and Philadelphia, with Mr Hudson’s curated guide.

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Philadelphia | Photo: Chris Murray

Jump off from Baltimore, Philly or DC

The Virginia Eastern Shore and Delaware Peninsula is within reach of as many as three great American cities, making it the place to go for vacationers in the know. If you’re starting from Baltimore, busy yourself with some of the many things to do in Baltimore before leaving. Drink at Edgar Allen Poe’s go-to saloon bar, grab a fresh cut at an old school barbershop or tour the boutique district of Hampden. Those looking for a beach near Baltimore ASAP can either stick to the main coastline at Gunpowder Falls State Park or Hart-Miller Island State Park or cross the Chesapeake Bay Bridge onto the peninsula for the easiest access to St Michaels.

But Baltimore isn’t the only metropolis in the running, because both Philly and DC are also wonderful places to begin a coastal road trip. If you find yourself with one or two days to kill in these cities, discover what to do and what to see with our Philadelphia and Washington DC travel guides.

Photo: Nathan Dumlao

Photo: Lauren Stiles

Chesapeake Bay, the Eastern Shore of Maryland

Seventy miles from Baltimore and a hundred from DC, Chesapeake Bay meets Maryland’s sandy eastern shore, on an island peninsula packed with beaches, boardwalks and windswept natural scenery. A handful of charming historic towns serve guests with restored inns, B&Bs and local culture, particularly within the Chesapeake City Historic District or colonial-era Chestertown. For a diverse choice of day trip, you’ve got the nearby Canal Museum or the Blackwater National Wildlife Refuge to the south.

Photo: Franciele Da Silva

St. Michaels, Maryland

Less than two hours from Philadelphia and just a short ride from DC is the quaint shore town of St Michaels providing the perfect escape from city life, accessible via the Chesapeake Bay Bridge on the eastern peninsula. Founded in 1778 by the English, St Michael’s staid British history fuses with two centuries of maritime trade, to create a town known for both shipbuilding and fishing with a great many restored colonial buildings. A gentleman in the streets and a seafarer in the sheets, St Michael keeps the party classy with a close-knit community centred on Talbot Street.

For ultimate rest and relaxation, choose between beach days or boat trips along the Miles River. Alternatively, check out the Chesapeake Maritime Museum, a key cultural institution spanning 18-acres along the waterfront, helping to preserve the bay’s history and culture while showcasing the town’s seafood harvesting methods. The best way to learn about the town’s seafood however is to eat it, and thankfully, St Michaels is not short of a crab house or two. As well as museums and boutique shops, the town centre has many great restaurants, all serving up local delicacies of crab and oyster.

St Michaels | Photo: Robert Zunikoff

Photo: Tyler Nix

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This narrow stretch of wilderness between the Atlantic Ocean and Chincoteague Bay is a worthy detour, greeting visitors with grassy dunes grazed by wild ponies and salt marshes swum by waterfowl

Chesapeake Bay | Photo: NOAA

Assateague Island

On the western side of the peninsula about two and a half hours from Baltimore, lies the undeveloped beauty of Assateague Island state park. This narrow stretch of wilderness between the Atlantic Ocean and Chincoteague Bay is a worthy detour, greeting visitors with grassy dunes grazed by wild ponies and salt marshes swum by waterfowl. Enjoy a beach day beside the 18th-Century lighthouse or explore the biodiverse waters off the coast for phytoplankton phenomena which attract a ton of marine life, including sea turtles and whales.

To get the best sightings of Assateague’s horses, deer, elk and more, take a boat or wildlife bus tour around the islet. Other activities on Assateague state park include hiking or mountain biking on island trails, or birdwatching, crabbing, clamming and fishing. The ecosystem on Assateague is both unique and treasured, meaning that at certain times of year beaches can be closed for bird nesting. As for the weather, Assateague summers tend to be both hot and humid while offseason can get overly windy. Bugs are a nuisance all year round here, so pack bug spray and protective clothing if you’re planning outside adventures. Find out more about the conditions on Assateague, at the National Park Service website.

Assateague Island | Photo: Skeeze

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A little further south on the Virginia Eastern Shore, road trippers will find the small island of Chincoteague which links to both Assateague and Wallops Island


A little further south on the Virginia Eastern Shore, road trippers will find the small island of Chincoteague which links to both Assateague and Wallops Island. With a Native American name that translates as “beautiful land across the water”, it’s hard to go wrong in Chincoteague as you’ll never be far from both wild ponies and super fresh oysters. If you’re lucky enough to visit in July, catch the annual pony swim when the local horses are herded across the Assateague Channel at low tide.

Tranquil on its busiest days, Chincoteague also offers adventure by way of horseback riding, boating kayaking, paddle boarding and swimming. Other things to do in Chincoteague include hiking or biking over 15 miles of trails within the nearby Chincoteague Island National Refuge which is home to over 300 species of bird. Chincoteague Beach is just a short mosey from downtown but those looking for a place to stay and a bite to eat should find the intersection of Maddox Boulevard and Main Street where most hotels, restaurants and shops are located. The food trucks dotting the roads will surprise you with the variety of food on offer, with everything from fresh local seafood and BBQ to Mexican and Vietnamese fare, with top-notch ice-cream and croissants for dessert.

If you happen to be a fan of space travel, don’t miss NASA’s Wallops Island Flight and Visitor’s Centre whose huge space satellites and rockets are visible from the road. Plan your trip around a rocket launch for a nerd’s dream come true! For more insight into the best Chincoteague Island things to do in each season, visit the local guide website.

Chincoteague | Photo: TM Parker

Chincoteague | Photo: Skeeze


A small state sharing half of the Virginia-Maryland peninsula, Delaware is an underrated destination perfectly positioned for a weekend getaway from its neighbouring flagship cities. Taking up the eastern part of the peninsula, Delaware lays claim to many of the region’s best beaches and colonial landmarks. One of the top things to do in Delaware is to slowly make your way down the coast, relishing in the region’s sparkling beaches (below) and chill atmosphere.

Rehoboth Beach

Said to be among the cleanest beaches in the country, Rehoboth Beach – just 2.5 hours from DC – is a crowd-pleaser both for families and the LGBT community. Known as Delaware’s top gay friendly beach spot, with an old school boardwalk and year-round events, Rehoboth keeps visitors entertained both day and night. Arrive early for a chance to watch the sunrise over Cape Henlopen State Park before lounging at the beach and refuelling on the town’s famous saltwater taffy and French fries (not together!). Adventurers will be pleased to know that Rehoboth is also down with kayaking, paddle boarding, sailing and surfing. Gordons Pond and the neighbouring forest are dream locations for hiking and biking excursions, while the wetlands and dunes looking out over the Atlantic Ocean makes for a great photo.

Once the sun sets, Rehoboth Avenue becomes popular, hosting karaoke bars, fine dining and local theatre productions from Clear Space Theatre (staging Broadway musicals for summer and holiday events!). Baltimore Avenue is also worth checking out, notable for nightly entertainment held at the Blue Moon Bar as well as al fresco dining at Aqua Grille. If you have interest in the local gay community, stop at CAMP Rehoboth for information on upcoming LGBT community events and many more things to do in Rehoboth.

Photo: Oliver Ragfelt

Bethany Beach, Delaware | Photo: Josefina Lacroze

Bethany Beach

While there are a number of coastal communities either side of Rehoboth – including Lewes, Dewey Beach and Fenwick Island – travel south a little to find the stand-out Bethany Beach. Come in the late afternoon just in time to catch a sunset water taxi, coming back to shore to discover Bethany’s historic charm, tax-free shopping and perhaps a sell-out summer concert. Pushing low-key vibes and old-world fun, Bethany Beach is worth the journey even if just to escape the crowds further north.

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Photo: Jessica Scrimgeour

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