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Follow Me to Chincoteague

Looking for a beach getaway that offers a change of pace? Here’s my guide to making the most of Virginia’s wild and wonderful beach destination, Chincoteague.

Much to my family’s embarrassment, I always ask Amish or Mennonite visitors in Chincoteague, Virginia, where they are from. Most say “Pennsylvania,” and when I explain I live in New Holland, there is instant amity. I have met folks from Gap, Leola and other places around Lancaster County in Chincoteague.

“Chincoteague is still a family-friendly community,” explains Joanne Moore, executive director of the Chincoteague Chamber of Commerce. “Obviously, we’ve changed over the years, but the Amish community still feels comfortable coming here. They are going to be respected and welcome.”

I get many comments on social media when I post pictures of wild ponies, quiet beaches and my favorite highlight, ice cream. So, to help anyone planning a trip to The Tump, which is Chincoteague’s unofficial nickname used by old-school residents – meaning “a small, rounded hill or mound” – here is a starter guide to my favorite beach vacation spot.

GEOGRAPHY BASICS

The island of Chincoteague was originally used as free-range grazing land for livestock, which gave rise to the tradition of “penning” animals each spring so that farmers could claim their herd members. The name of the island is derived from a Native American word that means “beautiful land across the water.” Photo: Chincoteague Chamber of Commerce

Chincoteague is a town of 3,000+ residents built on a barrier island on the Eastern Shore of Virginia, 200 miles south of Lancaster City. A sister barrier island, Assateague, is a National Seashore and straddles Virginia and Maryland, with the southern portion designated as a National Wildlife Refuge. There is a distinct difference between the two sides of Assateague, with the northernmost point ending at the Ocean City, Maryland inlet, while the Virginia side is known for its wealth of flora and fauna.

PONIES

They’re off! The ponies of the Southern Herd begin their swim across the channel as part of the annual Chincoteague Pony Swim that will celebrate its 100th anniversary July 30-31. Photo: Eastern Shore of Virginia Tourism

Made famous by the 1947 novel, Misty of Chincoteague (and subsequent film), the wild ponies of Assateague are a top tourist draw. The most famous explanation for the fuzzy, wide-bellied ponies’ existence involves their predecessors having survived the shipwreck of a Spanish galleon centuries ago.

The Chincoteague Pony Swim, held the last week of July since 1925, helps to manage the southern herd of wild ponies. Spectators (as many as 30,000) watch from Memorial Park and other points as ponies swim across the channel to Chincoteague, where they are led by Saltwater Cowboys (fire department personnel) to the carnival grounds. The next day, an auction is held, with foals fetching anywhere from $2,000-$8,500. Proceeds (last year’s event raised nearly $550,000) support the fire department.

The Chincoteague pony became an official registered horse breed in 1994. Photo: Michael Upton

Sharing everything about the pony swim, the history of firefighting on the island, and the month of activities at the carnival would fill these pages alone. (FYI: Garden & Gun magazine has a comprehensive article on the event in its June-July issue that even contains a shoutout to Lancaster.) Still, as this marks the event’s 100th anniversary, it’s worth noting that the aftermath of two devastating fires in the early 1920s spawned the creation of the Chincoteague Volunteer Fire Company. In need of funding, the idea for the carnival and pony swim was born. The organizers were shocked to see 15,000 spectators show up. The rest, as they say, is history. For some, the pony swim is an experience of a lifetime. For others, it is an annual ritual.

OYSTERS

The Chincoteague Oyster Festival will take over Tom’s Cove Park on October 11. Photo: Michael Upton

The island’s other famous creatures are Chincoteague oysters, known for their salty and clean ocean flavor. The oyster industry – now just a “shell” of its former self – dates to 1864 and currently survives on ecological planting and harvesting methods.

To dive into some oysters, check out happy hour at Chattie’s Lounge (located above Don’s Seafood Market & Restaurant) or shuck your own after visiting Gary Howard Seafood or Seabest Seafood Market. To learn more about these delicious bivalves, the 2-hour, interactive Shellfish Tour offered by Cowboy Cruise Company takes guests by boat to oyster-growing locations. The company, a Beacon Award nominee for Emerging Business, shares their aquafarm experience from seed to shuck, and guests can walk away with the freshest shellfish on the island.

ICE CREAM

There are three distinct destinations when it comes to ice cream on the island. Island Creamery offers a creative selection of handmade flavors like cantaloupe, bourbon caramel crunch and java jolt (coffee ice cream with brownie chunks and chocolate-covered espresso beans). Wendy Massey had the idea of turning her homemade cookies into ice cream sandwiches and BYOC (Build Your Own Cookie) was born; look for her truck on the island’s main thoroughfare, Maddox Boulevard. Soft serve is king at Mister Whippy, which started selling cones for a nickel back in the ’50s.

EATS and DRINKS

Capt. Zach’s is known for its “meal-sized” Bloody Mary. Photo: Michael Upton

Chincoteague’s first food truck, Woody’s Serious Food, is a testament to success; over the years businesses such as Having a Meltdown, Shark & Manders and Better. have joined a delicious food truck scene. Eateries like Pico Taqueria have moved from food truck to brick-and-mortar, while venerable spots like Steamers Restaurant & Sports Bar and Don’s Seafood Market & Restaurant continue to please crowds. Bill’s Prime and AJ’s on the Creek offer elevated dining experiences. One of the hottest “newer” spots on the island is Capt. Zack’s, a seafood purveyor turned beach-themed eatery that serves a meal-sized Bloody Mary (by special request).

If visiting during the off-season, swing into the Chamber of Commerce welcome center on Maddox Boulevard and pick up a list of open restaurants conveniently provided by local foodie Deanna Bredbenner, who posts as “A Girl Loving Food on Chincoteague” on social media.

THE BEACH

LOVEwork is a project of Virginia Tourism that promotes the state’s family-friendly vacation destinations. In Chincoteague it takes the form of oversized Adirondack chairs that are 10-feet high and weigh over 500 pounds. Visitors are encouraged to take a seat, snap photos and share them via social media. Photo: Michael Upton

What is now the public beach on Assateague will soon be a thing of the past, as natural erosion is making it fiscally impossible to maintain it in its current location. After a joint study by the U.S. Fish and Wildlife Service and the National Park Service, a new route to the beach will parallel the park’s Wildlife Loop and end two miles north of the existing beach area.

“A new beach location is a bit of a contentious thing, but … one good storm and it is gone,” says Joanne. “There are mixed emotions, for sure.”

Construction is happening now with completion expected in April 2026. All amenities, like lifeguard towers, showers and bathrooms will move north next year.

STAY

Key West Cottages provide visitors with charming bayside retreats. Photo: Chincoteague Chamber of Commerce

Like any beach town, Chincoteague has its fair share of chain hotels and independent rentals. It also has nice spots for campers. However, the hottest new spots have a bit of flash. BluFin, located on the quiet, southern part of the island, offers waterfront pet-friendly bungalows and floating houses. When crossing the causeway onto the island, one of the first things visitors will spot are the pastel Key West Cottages, well-appointed bayside retreats that sleep two to five guests.

The Chincoteague Seafood Festival celebrated its 55th anniversary on May 3. The event features any and all things seafood, area artisans and live music. Photo: Chincoteague Chamber of Commerce

For those who want more of my take on Chincoteague (like why you need to attend the annual Seafood Festival that is held in early May, and where to drop off your recycling), find me on social media. Or head to the Chamber’s welcome center where you’ll find a new 24-hour digital kiosk to help with recommendations, trolley info and more. Who knows, maybe I will see you around The Tump.

For more information, visit Chincoteaguechamber.com.  

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  1. I think this was a comprehensive article on Chincoteague, as I am a constant traveler there from Delaware. One interesting fact How did the horses get there originally? There has been many speculations. But just a few years ago , a DNA tooth on a ancient horse found in the Caribbean that came from Spanish galleons was linked to DNA of Chincoteague horses giving credence to the long romanticized explanation for The horses origin from a capsized Spanish ship.