For the 50+ Traveler

Virginia’s answer to island living is the unspoiled nature of Chincoteague Island. Home to the wild Chincoteague ponies, the island offers a rich history, gorgeous beaches, spectacular sunsets, and a wealth of wildlife.

Chincoteague Island is the southern gateway to Assateague Island and the Assateague Island National Seashore. It is situated in Chincoteague Bay about an hour south of Ocean City, Maryland.

It’s a mystery how the famous Chincoteague ponies came to live on the island, and there are several conflicting theories. The ponies were first made famous by Marguerite Henry’s Misty of Chincoteague. Published in 1947, the story revolves around a wild pony who eludes the round-up each year and the man who desires to own her. Reading it before your vacation will bring Chincoteague to life.

Here are 11 of the best things to explore on quaint, beautiful Chincoteague Island.

Wild ponies in the Chincoteague National Wildlife Refuge.

1. Chincoteague National Wildlife Refuge

The Chincoteague National Wildlife Refuge houses one of the herds of the island’s wild ponies. The Chincoteague Volunteer Fire Company purchased one of the two herds of ponies prior to 1943. The firemen continue ownership to this day and have a special permit to graze 150 ponies on the Chincoteague National Wildlife Refuge.

The refuge is home to diverse wildlife due to its multiple habitats. The ponies can be found on the beach, but you’ll also find many different birds including the migrating, federally endangered peregrine falcons who arrive in late September and October. The dunes offer nesting grounds for the piping plover and other shorebirds. The shrubs are home to many migrating and nesting birds, as well as migrating monarch butterflies who visit between mid-September and mid-October. The maritime forest protects forest wildlife such as the sika deer, the endangered Delmarva Peninsula fox squirrel, and others. Finally, the salt marshes are home to black ducks and other waterfowl.

2. Refuge Trek

The Refuge Trek across the 8-mile Northern Over Sand Vehicle Access Road will provide you with a unique view of Assateague Island. The tours are led by a wildlife expert from the Chincoteague Natural History Association and will bring you to a remote area on the island where you can discover local wildlife and ecology. You just might see Chincoteague ponies, white-tailed deer, sika deer, and other wildlife and birds on this small-group tour.

Food from the Ropewalk in Chincoteague.

3. Seafood Samplers

To-go lunches give you extra time to explore. Try Ricky’s Seafood and Produce Market for an order-ahead lunch. The single fried oyster basket with hush puppies is a favorite. Another great option is the soft crab sandwich -- crab is a must-try in this area.

For a classic on-the-water dining experience, visit the Ropewalk. The Ropewalk offers indoor dining, but also toes-in-the-sand booths and tables for the true beach dining feel. Try the Murphy’s mac and cheese loaded with shrimp, crab, pasta, and Cheddar sauce. For an even heartier meal, tuck into the Deadliest Steam Pot crammed with snow crab, shrimp, corn, potatoes, and andouille sausage.

The Pony Swim in Chincoteague.

4. Pony Swim

Each July, the Chincoteague Fire Department rounds up the ponies and foals in anticipation of the Chincoteague Island Pony Swim and Auction. The Saltwater Cowboys begin rounding up the ponies on the southern end of the island, eventually containing them within the Southern Corral. The next day, they round up the northern herd, penning them into the Northern Corral. On the third day, at dawn, the Saltwater Cowboys drive the ponies along the shore from the Northern Corral to the Southern Corral. All the ponies are examined by a veterinarian to ensure their continued good health.

The weeklong pony penning is accompanied by the Chincoteague Volunteer Fire Company Carnival, a classic, old-fashioned festival with rides, games, raffles, and great food.

Then, in a grand spectacle, the ponies, accompanied by the Saltwater Cowboys, swim from Assateague Island to Chincoteague Island across the Assateague Channel. The time of the Pony Swim changes yearly and follows the slack tide, which is the time between the tides when there is no current. The first foal across is named King or Queen Neptune and is given away in a raffle drawing.

5. Pony Auction

The culmination of the events is the Pony Auction. To keep the herd size under control, the foals are auctioned off, with the proceeds supporting the Chincoteague Volunteer Fire Company.

Each year, the Fire Company chooses several ponies to be buy-back ponies. These ponies are auctioned off with the understanding that the buyer will donate them back, ensuring a strong and diverse herd. For their donation, the buyer may name their pony.

On the last day of the festival, the ponies cross the channel and back to their designated area, where they live in freedom for the rest of the year.

A boat tour with Daisey's Island Cruises.

6. Island Boat Tours

The best way to understand an island is to view it from the water. Daisey’s Island Cruises offers visitors a chance to experience island life firsthand. On their 2-hour, small-scale Scenic Pontoon Tour, you can view the ponies up close in their natural habitat.

If you are planning on visiting Chincoteague Island during the annual Pony Swim, Daisey’s offers a Swim With Wild Ponies tour. Imagine floating in the water with an up-close view of the ponies swimming by your boat. It’s a unique adventure not experienced by many visitors.

7. Kayak Tour

Do you prefer to power your own adventure? Then you might want to give the Assateague Explorer Kayak Tour a go. As you paddle through the backwaters of the islands, you’ll have an opportunity to quietly explore the Chincoteague National Wildlife Refuge and view the ponies from a short distance without disturbing their day. The guided tours are perfect for all kayakers, from beginners to the experienced. The knowledgeable guides know where the local wildlife is nesting, resting, and dining, making for a fantastic nature-driven adventure.

The NASA Wallops Flight Facility in Virginia.

8. NASA Wallops Flight Facility

The NASA Wallops Flight Facility is a center for research, satellite tracking, scientific investigations, technology development, and commercial aerospace. The visitor center offers educational programs for aerospace geeks and curious space explorers alike.

9. Cottages On Stilts

When you’re in the area, consider staying in a cottage on stilts with an expansive porch right on the water. Key West Cottages on the Chincoteague Bay is a great place to start looking. Imagine sitting on your private deck with your favorite cocktail in hand while watching the watercolor sunset over the bay, listening to the quiet lapping of the water, the dusky sounds of shorebirds, and the gentle whisper of the bay breeze.

Shops along Historic Main Street in Chincoteague.

10. Historic Main Street Merchants

The Historic Main Street Merchants of Chincoteague take great pride in the history of their town and the quality of their merchandise. On this lovely street, you will find one-of-a-kind shops that offer visitors a peek into Chincoteague’s past. Don’t forget to pick up a copy of Misty of Chincoteague while you are downtown. It would make a great souvenir!

The Chincoteague Step Through Time Tour is a fun stroll through the downtown area on which your guide will explain the legends and lore of the island. The tours run several times each day, but the 7 p.m. tour has a special feel -- you’ll walk through the town as the sun sets, providing a gorgeous backdrop.

11. Beaches

The beaches at the Chincoteague National Wildlife Refuge are some of the most beautiful on the East Coast. Pack a picnic and spend the day basking in the glorious Virginia sunshine.

The recreational beach is the main beach at the refuge and is a swimmer’s paradise. Wild Beach is an 11-mile-long stretch that entices hikers to take to the sand and walk, walk, walk. The beaches of Toms Cove Hook and Assawoman, Cedar, and Metompkin Islands are open only sporadically in order to protect endangered species. These out-of-the-way oases are worth seeking out during your visit.

What To Know Before You Go

If you are interested in attending any of the special events surrounding the Pony Swim and Auction, you’ll need to book at least one year in advance.

You can drive around town and see one or two ponies by the sides of the coastal roads. However, the best way to view them is on a tour. The guides will know where the largest herds are grazing, offering a once-in-a-lifetime view.

If you have more time to explore the area, consider traveling north to Maryland or Delaware. The Delmarva area has so much to offer -- it is always worth a visit.