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3 May 2022
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For an island that is only seven miles long, by one and a half miles wide - Chincoteague has a lot of nooks and crannies to be explored. It's easy to look at a map, but we thought we'd give you a general lay of the land here on the blog - along with all our favorite things to be found along the way. Hopefully it may help you find something new to fall in love with here on Chincoteague Island.

The hub of the island is Maddox Boulevard, or "Beach Road" as locals like to call it. It's a straight shot from the bridge to the beach, and you'll pass countless cafes, restaurants, an AWESOME vacation rental office (wink, wink!), and activities along the way. Crossing the next bridge will take you to Assateague Island National Seashore, where you will find expansive stretches of undeveloped coastal forest and coastline. You will also find our photogenic and very active lighthouse. There's a short trail that leads you to the base (pack your bug spray in summer), and if you go at dawn or dusk (when the lights are still on), you can get some really cool photos from the base.

Ponies can usually be seen in the stretch of marsh in between the lighthouse trail and the actual beach, on your right hand side if you're heading towards the ocean. It's a great place to pull off for a photo op as there is plenty of shoulder space on the road. 

The wildlife loop is also wonderful, but only open to vehicles after 3 PM. Spanning 3 miles, it's a great walk or bike ride too, and open all day for those activities. You'll see tons of wildlife along the way, and there is a trail off of the wildlife loop that gives you beach access further north - great to get away from folks or to do some serious beachcombing. Less people equals more treasures for you!

Back on the island, if Maddox is the hub - Main Street is the heart. Our charming small-town downtown offers shopping and dining, a knockout view of the Chincoteague Channel, the LOVE chairs (that make such a cute Insta), and a public dock that's a great fishing spot. You'll also find a public boat ramp right in town. Main Street is the only road that stretches the entire length of the island. 

At the northern end you'll find Capt. Chandler, the gravesite of an old sea captain with an odd epitaph - you'll have to drive down and visit him for yourself. It's tradition to leave a coin or a seashell as a token. The best sunsets, cocktails, and nightlife can be found further down on Main - drop by Chincotiki, Chatties, or Ropewalk to check out the island vibes.

Mid-way on Main you'll find the carnival grounds, which is where much of the shenanigans of Pony Penning take place. Drop by for the best oyster fritter if they're open! And finally, down at the southern end you'll find Curtis Merritt Harbor - the gold standard for your sunset photos (no pun intended). 

Many of the boat tours meet at the harbor, and that's always a great activity to plan for. It really is the best way to see the island!


Along the backside of the island you'll find Eastside Drive. Our aquaculture capital here on the island. You'll find several oyster processing houses, which sell to the public. Memorial Park is also located just off of Eastside. It's a great spot for sunrise photos if you're not feeling like going all the way to the beach. Your best view of the lighthouse is also found on Eastside Drive, well - that can be found on Chincoteague Island.

Ridge Road and Willow Street kind of cut through the middle of the island horizontally, and don't feature a ton of businesses - just sleepy residential neighborhoods for the most part. Great for riding the bike or jogging. Swing by Ridge Road Pit Stop to grab a cup of coffee or a cold bottle of water.

Church Street cuts through vertically, and features our beautiful historical churches. Our farmers market can also be found on Church Street, along with the locally owned and operated hardware store and a couple of great shops. Make sure to go see Jerry & Paula for a tomato pie at Church Street Produce.

Last but not least, Deep Hole Road. Some might wonder why such a strange name? In the waterway just off the road there is a deep hole - old times say it used to be 80 feet deep. Now it's at about 35 feet, being filled in over the years with our shifting shoals. It was made millions of years ago when a piece of meteor slammed into the Earth, a chunk that broke off of the large one that landed just off of Cape Charles that helped form the Chesapeake Bay as we know it. Little history lesson for you!

Deep Hole Road offers the best seafood options on the island - one being Captain Zack's for their seafood market and awesome prepared seafood offerings!

The town dump and recycling center is also located on Deep Hole Road (closed Tuesdays) and Hallie Whealton Smith Drive is located off of Deep Hole as well. You'll find our local dog park as well as two beautiful nature trails for your enjoyment.

There are plenty of roads and drives that didn't make the list - but get on the bike and explore for yourself. You will no doubt find something enchanting in your travels. Enjoy getting on island time!