48 hours in Chincoteague Island

by Michael C. Upton  |  Published November 20, 2020

South of where nightlife and neon dominates the Atlantic Coast of the Northeast “island time” is real, and days seem to go as slow as the 25-mph speed limit set throughout Chincoteague Island. There are no amusement park rides, no boardwalks. Relaxation takes center stage, and there is plenty of fun to be had and adventures to be made during a 48-hour stay.

Natural spectacle on Chincoteague Island, Virginia (Photo: Michael C. Upton for

The barrier island, home to the Virginia town of Chincoteague, is nestled between the mainland and Assateague Island National Seashore and gets its name from the Gingo Teague tribe of Native Americans who hunted nearby. Built on the blue-collar traditions of fishermen and women, Chincoteague is renowned for its oysters, which thrive in the salty bays. But bivalves are not the only creatures that lure hundreds of tourists to the island every year.

Wild ponies make their home on Assateague Island (Photo: Michael C. Upton for

Many folk tales tell stories of the wild ponies roaming Assateague Island. Some say they were released by early settlers. The most widely accepted account of the fuzzy, wide-bellied ponies’ existence makes them survivors of a Spanish galleon wrecked off the coast. Today, 150 of these ponies are property of the Chincoteague Volunteer Fire Company and their Saltwater Cowboys. To keep the herd manageable the fire company holds an annual pony auction.

The famous “salt water cowboys” swim the wild ponies from Assateague to Chincoteague (Photo: Michael C. Upton for

Far from the nearest inland town in 1920 and 1924 when major blazes torched much of Chincoteague, the fire company needed a way to raise capital for equipment and the pony sale fills the need. To get the wild ponies from Assateague to the fairgrounds on Chincoteague the Saltwater Cowboys conduct an annual Pony Swim, drawing approximately 30,000 to 40,000 visitors to the island of 3,000 residents.

The Pony Swim and auction punctuates the festivities of the Annual Chincoteague Volunteer Fire Company Carnival, which runs through the entire month of July and features rides, games, and food—especially seafood—for the entire family. Generous volunteers run the event where kids walk away with plenty of prizes and fond memories.

No boardwalks, no amusement parks, and nature is key on Assateague Island, VA beach (Photo: Michael C. Upton for


In the entire history of ponies on Chincoteague, Misty is the most famous. She is the subject of the 1947 book “Misty of Chincoteague” by Marguerite Henry, a story engrained in the modern persona of the island. Where she lived, the Beebe Ranch (3062 Ridge Rd), is still around and attracts dedicated visitors daily. Taxidermized, Misty remains on the island today and can be visited at the Museum of Chincoteague Island (7125 Maddox Blvd). In 1961 the story spawned a film, “Misty”, and it still shows at the circa-1945 Island Theatre (4074 Main St). Take a look on the pavement out front of the theater to see the star’s hoofprints.

A statue of the island’s most famous pony, Misty, is located downtown (Photo: Michael C. Upton for

Protected by a National Wildlife Refuge the ponies live in a pristine, natural habitat also appreciated by human visitors looking for seashell studded beaches, windswept dunes, and authentic nature trails. The beach—accessed in Virginia only via the Chincoteague causeway—opens to visitors as early as 5:00 a.m. EST in the summer months. During peak months, visitors begin to pack the beach around noon.

Assateague beach is home to many activities including surfing, fishing and kayaking (Photo: Michael C. Upton for

Beyond beachgoers, Assateague attracts sportsman for tide fishing and seasonal hunting, nature lovers and families who enjoy the Toms Cove Visitor Center (open year-round and offering seasonal park activities), and lighthouse tourists who come to see the 142-foot-tall beacon of Assateague Lighthouse. Climbing the 175 steps to the top of the structure is strenuous due to the narrow design, which was completed in 1867 after a construction hiatus due to the American Civil War.

Visitors can climb the 175 steps to the top of the Assateague lighthouse (Photo: Michael C. Upton for

Back on Chincoteague a beach economy thrives on tourism. Downtown Chincoteague has been circumvented by heavy traffic and specialty shops line Main Street. Maddox Blvd. is the main thoroughfare connecting the causeway to the beach and is dotted with shops peddling beach supplies and souvenirs, rental agencies for bikes and motorized scooters, and mainstays like banks, pharmacies and gas stations.

Virginia is for Lovers. And so is Chincoteague. The state slogan lives on in this coastal community where visitors to Robert Reed Waterfront Park can opt for an Instagram moment on four oversized beach chairs. The park also offers a spot to relax and watch boats head to and from fishing spots on Chincoteague Bay.

The “love chairs” are a wonderful photo opportunity (Photo: Michael C. Upton for

Dating to the 1800’s, the Captain Timothy Hill House (5122 Main St) is the oldest home on Chincoteague Island. Constructed when houses on the island were few, it managed to be spared the ravages of time by hiding under newer construction. Peering through the windows reveals hand carved images of wooden ships in the one-story building’s beams. The Captain Timothy Hill House was registered as a Virginia Landmark and placed on The National Register of Historic Places in 2011.

Hungry visitors come for the Chincoteague Seafood Festival each May (Photo: Michael C. Upton for

While most visitors come for the ocean and the ponies, annual events like the Chincoteague Seafood Festival in early May and the Chincoteague Oyster Festival in October draw visitors to the island during the off-peak season. And it is a merry time at the beach over the winter holidays, too, when the town hoists beach-themed ornaments up onto the light poles and drops a glittering horseshoe at midnight on New Year’s Eve.


Rough camping is allowed in the Assateague Island National Seashore, but for less rustic accoutrements, Chincoteague Island has more offerings. Tom’s Cove Park (8128 Beebe Rd) is the most recognized campground on the island and is closest to the annual Pony Swim; the event can be witnessed from several tent sites and the park’s fishing pier.

For a short trip to the island a night at an inn or hotel will suffice and there are plenty on the island. Marina Bay Hotel & Suites (3801 South Main St) is the newest accommodation on the island, is Chincoteague’s first boutique hotel, and prides itself on luxurious guestrooms and four-star amenities.

Families looking for extra fun pack into the Chincoteague Island KOA Resort (6742 Maddox Blvd), which added a waterpark to their list of amenities in 2018. Meanwhile, Comfort Suites (4195 Main St) was remodeled in 2020, including guest rooms, the lobby, and the indoor pool.

Rental homes like Heron Creek are great for longer stays (Photo: Michael C. Upton for

The most pleasant way to spend more time on the island is to rent a home. Chincoteague Resort Vacations (6426 Maddox Blvd) and other rental companies on the island offer a variety of locations for boaters, beachgoers, or for those simply looking to relax.

Luxury is key at Heron Creek (7139 Silver Sails Landing), situated in a quiet neighborhood within walking distance to the fairgrounds and downtown. This rental home offers paddleboat and kayak fun, modern amenities inside, an outdoor pool, and it is dog-friendly!


Get up early for a visit to Sandy Pony Donuts (6300 Maddox Blvd), who offer extravagant fried delights made to order until noon. The 24-donut menu features standouts like the Porky Pony (honey glaze, cinnamon sugar, and bacon), the Yabba Dabba Doo-Nut (topped with Fruity Pebbles cereal), and the Chocolate Covered Pretzel donut.

Seafood is on every menu, like these ahi tuna tacos at Ropewalk (Photo: Michael C. Upton for

The beach life is transported to casual dining at the Ropewalk (6262 Marlin St.) where picnic tables in the sand overlook the narrows with great sunset views. Pico Taqueria (6560 Maddox Blvd.) started as a shack-kitchen, but their popularity helped them grow into a brick and mortar establishment offering both indoor and outdoor seating to enjoy gourmet tacos.

Outdoor dining is fully embraced in Chincoteague and a few spots have made it their specialty like Woody’s Serious Food (6700 Maddox Blvd); the hippie-themed eatery focuses on traditional southern bbq and fun with family games and artistic curiosities sprinkled about the property.

Fine Dining on the island is punctuated by Bill’s PRIME Seafood & Steaks (4040 Main St.). Operating since 1960, Bill’s, of course, specializes in fresh, local seafood and hand cut steaks. Meals can start with a throwback to yesteryear with the house tropical shrimp salad and include perennial favorites like Smothered Flounder, Herb Roasted Prime Rib, or the Broiled Seafood Feast. The cocktails at Bill’s are made with quality craftsmanship and the wine list boasts four pages of reds, whites, and sparkling varieties both local and from around the world.


Much of the allure drawing visitors to this area centers on the mostly unspoiled natural surroundings. Whether it is wild ponies, bird watching, fishing, etc., the nature lover is going to find Chincoteague the gateway to an earth friendly vacation. Here’s just a few ways to get started.

Nature walks on Assateague can led to wonderful experiences (Photo: Michael C. Upton for

Take a hike. There are six hiking trails maintained by the Chincoteague National Wildlife Refuge. The largest trail is the 3.25-mile paved and wheelchair accessible Wildlife Loop. Spot waterfowl in the winter and shore and wading birds in the summer. The trail is open to walkers and bikers all day. One of the most visited nature hikes is the Island Nature Trail (Hallie Whealton Smith Dr), a paved, 1.4 mile loop on Chincoteague Island, which is often quite buggy; across the street is an unpaved trail, too. The Chincoteague Chamber of Commerce ( provides a walking and biking tour map for visitors.

Take a ride. Seeing the island from the water puts a visit in a whole new perspective. Captains from tour companies like Daisey’s Island Cruises (4103 Main St) work together to provide the ultimate experience for marine life sightings and pony viewing. Most captains have a vast knowledge of the history of the island and surrounding waterways and are eager to answer any questions. For do-it-yourselfers, the island has five public boat launches. Kayakers can access the Virginia Seaside Water Trail at a number of places on and around the island.

Island tours by boat are a great way to see the area (Photo: Michael C. Upton for

Enjoy stellar views. Chincoteague Island’s proximity to NASA’s Wallops Flight Facility gives visitors the chance to view a rocket launch. Wallops serves as a cargo refueling command for the International Space Station and periodically sends unmanned rockets into space. Getting to Chincoteague takes visitors right past the NASA Wallops Flight Facility Visitor Center (Building J20 Route, 175 Chincoteague Rd, Wallops Island).


A trip to any seaside destination is never complete without some ice cream. In Chincoteague, the frozen dessert is dominated by two entities within walking distance of each other and always featuring a line of patient patrons.

Mr. Whippy (6201 Maddox Blvd) is the place for soft serve—and only soft serve. The legend of Mr. Whippy begins in the 1950s when an ice cream cone coast a nickel and the business grew from a backyard endeavor to the full-blown attraction of today. Beyond cones and milkshakes Mr. Whippy ice cream makes incredible specialty sundaes and candy/ice cream mashups called Cyclones.

All of the hard-dipped ice cream at Island Creamery (6243 Maddox Blvd) is made on premises and some of the flavors are seasonal delights. But the biggest draw here may be the fresh, crisp, and handmade waffle cones—they are so popular bags of broken “seconds” are sold for a couple bucks. Island Creamery’s flavors are often outlandish and uber-decadent. For instance, the popular Java Jolt is a strong coffee ice cream with brownie chunks and chocolate covered espresso beans. The Cherries Jubilee is brandy flavored ice cream with cherries heavily soaked in brandy. A springtime favorite flavor is Cantaloupe.