Back To Blog

Plan Your Fall Getaway to Chincoteague

Plan Your Fall Getaway to Chincoteague

I want to do more posts about day trips and weekend getaways since there are so many wonderful destinations in Delaware and the adjoining states. Places you can drive to in two hours or less, with charming accommodations, wonderful restaurants, quaint shops and scenic wonders. This week I’m focusing once again on Chincoteague, Virginia. Here are some high points:

It’s comprised of two connected islands with peaceful bay views on one side and the roaring Atlantic ocean on the other. The first island, Chincoteague, is reached via a long causeway just a few feet over that bay. Once you’re there it’s easy to see the whole island along with the adjacent Assateague Island via your bike or with leisurely drives. There aren’t any hills on the islands, so biking and hiking are super easy.

You can encounter wild horses on Assateague. Assateague Island is where you’ll go for ocean waves. The whole place is a vast nature preserve, with hundreds of acres of woods and wetlands that you can view from biking and walking paths. The island is famous for the wild ponies that first appeared there in the 1700s. Some believe they swam ashore from a Spanish galleon that wrecked on the island; others say it’s more likely they were herded onto the island during colonial times by farmers who wanted to avoid mainland taxes. They’re a beautiful sight as they move leisurely along the beach – often with just a few feet of people during the summer. 

It's a charming town for old house fans. The island has lots of lovely Victorian-styled homes in the farmhouse vernacular style that can be found in older communities throughout Delaware, Maryland and Virginia. You’ll also find craftsman-styled cottages and homes from the 1920s and afterwards, along with more modern Colonial styles. In town they’re all set close to the sidewalks that make the whole town so walkable, creating a very charming streetscape. A few of the grander homes have been transformed into hotels and B&Bs.

And a great destination for foodies who love seafood and local produce. Chincoteague has several wonderful restaurants specializing in seafood and steaks. Most offer simply prepared dishes with an epicurean flair, and you can count on fresh vegetables and other items from nearby farms. 

Bill’s Prime Seafood and Steaks https://www.billsprime.com/ has been serving since the 1960s and today offers home-style cooking with a fine dining vibe, including a rich and cheesy seafood Norfolk with local blue crab, shrimp and scallops, a rich Cioppino fish stew, and sizeable prime steaks. 

A.J.’s on the Creek https://www.ajsotc.com/ also offers abundant seafood dishes and lovely marshland views. You’ll also get wonderful seafood here, along with Angus rib-eyes, New York strip and filet mignon served with different sauces and, like Bill’s, a wide selection of good wines. There are many additional choices, and it’s a good idea to check out the full selection https://www.tripadvisor.com/Restaurants-g57602-Chincoteague_Island_Virginia.html and to make reservations ahead of time if you’re going to Bill’s or other popular places. 

The Island Theatre is an especially cool spot. Located on the main street downtown, it’s a perfectly preserved Art Deco treasure that features films some days and live entertainment on others. It’s a place of pride for many on the island who have contributed lots of time and effort to keep it going. Going there for a show after dinner is a true step back in time. 

Fall is a wonderful time to visit. The area is best known for the “Pony Swim” that happens every July when the wild horses are herded at low tide from Assateague to Chincoteague, then paraded through town to an auction that occurs the following day. If you visit then, you’ll need to plan well in advance if you want to stay overnight since most hotels sell out for the event. But you’ll find much smaller crowds in the autumn, with pleasant bay and ocean breezes adding extra zip to your long bike rides through town and through Assateague’s nature preserve https://www.nps.gov/asis/planyourvisit/take-a-bike.htm