On Virginia’s Eastern Shore lies the island of Chincoteague, gateway to the famous Assateague Island National Seashore and home to a tight-knit community with a rich history in the seafood industry. Chincoteague is a mere 4 hours from Washington D.C. and Philadelphia, yet the idyllic, quiet island feels like worlds away.
Chincoteague gained fame after the 1961 film Misty of Chincoteague, which highlighted one of its most well-known attractions, its wild ponies. To this day, Assateague Island hosts a herd of approximately 150 wild horses managed by the Chincoteague Volunteer Fire Company. While their origins are debated, many contest that the now aptly named “Chincoteague Pony” is a descendant of survivors of a Spanish shipwreck in the 1700’s.
Made famous by Misty of Chincoteague, the Chincoteague Island Pony Swim has been an annual event in Chincoteague since 1924. Held every July, “Saltwater Cowboys” round up the ponies to corrals for public viewing, and days later proceed to swim the ponies from Assateague Island to Chincoteague for a foal auction, which helps control the population and fundraise for the local Volunteer Fire Company. Visitors can book charter boats well in advance to witness this unique event up close, and each night also includes a carnival celebration, free to the public. The town also boasts a blueberry festival and farmers’ market that weekend for all to enjoy.
Even if you can’t manage to book a charter boat for the Pony Swim, there are plenty of opportunities to embark on guided boat tours and experience the abundant wildlife and unique ecosystem of Chincoteague and Assateague. There are over 15 boat tour companies in the area, and so much coastline to explore. If self-powered boats are more your style, you can rent a kayak on your own or join a Kayak Eco Tour to navigate the islands.
Sure, the beaches here are great, but in an area so rich with natural and cultural history, there’s also so much to learn! Take a trip to the Chincoteague Bay Field Station to participate in a hands-on Atlantic marine life workshop or family camp, or gawk at the North American River Otter exhibit at the Delmarva Discovery Center and Museum. If you can’t make it in July for the Pony Swim, you can still see (and even ride!) real Chincoteague Ponies at the Chincoteague Pony Centre. To discover more about Chincoteague’s vibrant past, trace its history at the Museum of Chincoteague Island for just $4.
Immerse yourself in Chincoteague’s unique maritime culture by trying your hand at clamming or crabbing. After grabbing your supplies at a local store such as Captain Steve’s Bait and Tackle, head over to Swan Cove or along Beach Road in Chincoteague National Wildlife Refuge, where anyone is allowed one bushel of blue crabs per day—that is, if you can catch them! In Toms Cove, bring a bucket and dig for all types of different clams, up to 250 per day. If you’re not that lucky, check out the Oyster Festival in October, or Seafood Festival in May.
Just about an hour north from Chincoteague is Ocean City, Maryland, a buzzing seaside center with 10 miles of beachfront at your fingertips. Check out the shops, amusement rides, and endless entertainment along its 3 mile-long boardwalk. Ocean City’s high energy environment provides the perfect contrast to the relaxed, small town vibes of Chincoteague, ensuring a fun, well-balanced vacation.
Inland from Ocean City is the largest city in Maryland’s Eastern Shore region, Salisbury. Grab dinner at one of the many area restaurants, see popular artists such as Chris Young at the Wicomico Civic Center, or stroll the art galleries downtown and ride the weekend Trolley down Main Street.
Tripping.com presents a wide variety of accommodations in Chincoteague Island, and since the town is only 7 miles long, you’re always close to anything you’d need! Check out places around Main Street to be near historic downtown—otherwise, Maddox Boulevard is a good bet if you’d rather be close to the beach.
To get to Chincoteague, visitors can fly into Wicomico Regional Airport in Salisbury, or to one of the 6 national and international airports, all less than 4 hours away. After you’ve arrived, the Pony Express will take you to most points of interest around the island for a mere 25 cents.
Find the best Chincoteague vacation rentals with Tripping.com. Choose from 125 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $25 a night to $3320 a night.
Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 93 of homes in Chincoteague offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 39 rentals with pool or jacuzzi, or relax with the family in one of the 96 homes with cable TV.
For all those dog lovers and cat lovers, Chincoteague offers 29 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.Search properties from 6 rental sites in Chincoteague where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 77 HomeAway rentals, 21 TripAdvisor short term rentals and 12 Booking.com vacation rentals.