Assateague Island, straddling Maryland and Virginia, draws visitors with its roaming wild ponies, pristine barrier beaches, and unspoiled coastal marshlands.
Assateague Island is a 37-mile barrier island shared between Maryland and Virginia, managed jointly by the National Park Service and the U.S. Fish and Wildlife Service. Its protected status has kept it largely free of the commercial development that defines much of the mid-Atlantic coast, preserving a landscape of rolling dunes, maritime forest, tidal flats, and open ocean beach that has changed little over centuries.
The island's wild ponies are its most celebrated feature. Descended from horses believed to have survived a colonial-era shipwreck or, more likely, placed on the island by mainland farmers to avoid livestock taxes, these small, sturdy animals have adapted fully to the coastal environment. On the Virginia side, the Chincoteague Volunteer Fire Company holds an annual pony swim and auction each summer, a tradition dating back decades that draws large crowds to the region.
Beyond the ponies, Assateague Island offers some of the finest undeveloped beachgoing on the East Coast. Swimmers, surfers, and anglers share the shoreline across different stretches, while birders find the island especially rewarding during spring and fall migrations. Overnight visitors can camp on the beach or in the pine forest, falling asleep to the sound of waves and waking to the sight of ponies grazing nearby.
Few places along the Eastern Seaboard offer such a direct encounter with a coastal ecosystem still operating largely on its own terms, which is what makes Assateague Island worth the trip for anyone drawn to natural landscapes.
Visit during late spring or early fall to enjoy milder temperatures, smaller crowds, and active wildlife along the marshes and shoreline.
Try surf fishing along the ocean side, where striped bass, bluefish, and flounder are commonly caught from the beach.
Bring insect repellent in generous quantities, as biting flies and mosquitoes are persistent from late spring through summer.
Rent a kayak or canoe to paddle the calm back-bay waters on the Maryland side, where herons, egrets, and shorebirds are plentiful.
Keep a safe distance from the wild ponies at all times and never feed them, as they are protected animals and can kick or bite without warning.
Parasail off downtown Ocean City with tandem or triple flight options
Rent a kayak or stand-up paddleboard from the beach at Aloft Hotel
Private 1-hour skiff cruise to Assateague Island for pony and wildlife spotting
Private Ocean City sunset skiff cruise for up to 5 from the Aloft Hotel
Book a private 1-hour happy hour cruise for up to 5 guests
Cruise Ocean City’s back bays and ocean on a private boat for up to 12
Private Ocean City & Assateague sunset cruise for up to 12
Cruise Ocean City harbor and see White Marlin Open yachts with your private captain

Cruise Ocean City on a tiki boat with included drinks, guided by a captain and bartender

Enjoy included drinks while a captain and bartender guide a 90-minute tiki boat cruise

Enjoy Ocean City waters with a captain and bartender, drinks included on a 90-minute cruise
Paddle from Chincoteague to Assateague to look for wild ponies and lighthouse views
Walk Chincoteague’s history and birdwatching spots with a local guide
Cruise at sunset to spot Assateague ponies and coastal wildlife
Find newborn foals and see as many pony herds as possible with a Saltwater Cowboy captain
Cruise Ocean City waters on a private tiki bar boat with captain, bartender, and included drinks
Charter the Calico Jack for a private bay cruise with space for up to 32 guests
Cruise Chincoteague waters and look for bottlenose dolphins (1.5–2 hours)
Cruise Ocean City’s bays at sunset with ghost stories and local lore
Cruise Chincoteague and harvest clams and oysters along the way
Cruise toward Assateague Island at sunset with a tiki-themed bar onboard
Watch Sunday night fireworks on a private bay skiff for up to 5 guests