In today’s Local Perspective, I’m chatting with Allie Tolbert of Allie Beckley Photography on everything she loves about Chincoteague Island, Virginia. Chincoteague Island is located on the Eastern Shore, nestled between the Virginia mainland and Assateague Island, and is a destination spot for campers, wildlife enthusiasts, and beach lovers alike. Sound like a place you’d like to visit? Read below for your complete guide on things to do in Chincoteague and tips on how to experience the Island like a local!
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Table of Contents
What to know about Chincoteague Island
I want to visit Chincoteague Island. What’s the best time of year to come?
The best time to visit based on the weather and tourist season is late May and September/early October. The shops and restaurants are open by Memorial Day, and since most schools are still in session, it’s not packed. Everything stays open until about the second week of October, so September/early October are also great times to visit while avoiding the crowds.
(Pro Tip: If you’re prone to mosquito bites, pack your bug spray! Those suckers can be vicious in the summer months!)
How easy is it to get a local experience?
Chincoteague is an insanely friendly small town where everyone knows each other. You’re not going to find any high-rise buildings or a bunch of chain stores. Therefore, you don’t have to look far to experience the Island as the locals do. If you carve out time to enjoy the beach, peruse the locally-owned shops on Main Street, and eat seafood, you’ll be living like the locals.
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Chincoteague Hotels: where to stay and how to get around
Do you have any recommendations for lodging?
Everything is so close, so you really can’t go wrong with a location. There are several hotel options on the Island. Hampton Inn & Suites, Comfort Suites, and Fairfield Inn & Suites are nice spots on Main Street. The Best Western is the closest to the beach, so if you want to be out of the main traffic area and have easier biking access to Assateague, this is the best bet. A lot of people forgo chain hotels and rent a house through Airbnb or other rental sites.
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Now that I’m here, how do I get around?
Bike. Bike. Bike. There’s also a trolley, and walking is not hard since the Island is only 3 miles by 7 miles, but biking is where it’s at. The speed limit is 25 mph, so driving is almost pointless. Please do not rent a scooter…
Chincoteague Restaurants: where & what to eat
What cuisine is Chincoteague known for and where do you get it?
Seafood reigns supreme here, oysters specifically. Come in the fall for the Oyster Festival to enjoy the best deal for eating local seafood. If you’re looking for a nicer, sit-down experience, check out Bill’s next to the old firehouse on Main Street (reservations recommended). Ray’s Shanty, off the Island, has the best bang for your buck. Lastly, Gary Howard Seafood (5315 Deep Hole Rd, 757-336-5178) is best to pick up and enjoy at home. It’s our go-to spot for a pound (or two) of steamed shrimp.
Sometimes the best places to eat are hard to find. Is there a place we should keep an eye out for?
There’s a food truck off the main stretch called Right Up Your Alley (2295 Main St) with authentic Brazilian cuisine. The food is great, and their prices are better than most food trucks on the Island, so it’s a win/win! Lily’s Little Mexico is another excellent food truck that offers authentic Mexican food at a reasonable price. You can find it at 6700 Maddox Blvd.
Here are a few other food options for the non-seafood lovers: Sea Star Cafe is awesome. Order at the counter and enjoy it on one of their picnic tables or take it to go. Everything is delicious, so you can’t go wrong! Pico Taqueria is a really good, unique Mexican stand. This is another order at the window and eat outside place. For breakfast, many people love the Sandy Pony Donut truck, but if you’re willing to take a little drive, head to Onancock to the Corner Bakery (36 Market St, Onancock, VA) for the best traditional donuts around. If you do head to Corner Bakery, you must swing by Crossroads Coffee Shop (25514 E Main St, Onley, VA 23418) for some coffee to compliment it. It’s located in an old bank and offers everything you could hope for in a small-town coffee shop: history, character, and an excellent cup of joe (bonus: there’s an old bank vault turned reading nook for the kiddos!).
Things to do in Chincoteague
I’m a first-time visitor. What’s the one thing I must see/do?
I can’t narrow it down to one thing, so here’s 3: You must have a Chincoteague Oyster, see a wild Chincoteague pony, and ride your bike to a bar. Oh, and you have to try either Island Creamery or Mister Whippy. Island Creamery is rated best ice cream on a ton of polls, but if you prefer soft serve, Mister Whippy’s it is!
Tell us about your favorite area/thing to do.
My favorite area is Assateague Island National Seashore (technically the Chincoteague National Wildlife Refuge, but you’ll likely hear it referred to as Assateague). There are a ton of trails, and if you hike far enough, you’ll encounter pristine, untouched beaches. A favorite of mine throughout the years has been to take the 3-mile Wildlife Loop and hit up the beach access there since it is far from parking (and tourist). However, they are prepping to put parking where the trail meets the beach, so my secret secluded spot may not be a secret for much longer.
How do you like to spend your weekends?
My favorite weekend activity is either bumming on the beach or going out on the boat. My husband is an avid water sports enthusiast (surfing, wakeboarding), so we spend a lot of time on the water. Take note, the beach is on Assateague Island, which is a National Park. A park entry fee is required to access the beach.
What’s your favorite “touristy” thing to do?
I love to see the ponies. They’re such beautiful creatures. In a world where true wildlife is becoming a scarce commodity, it is both reassuring and awe-inspiring to see these animals not only surviving, but thriving in their natural habitat! Head to Assateague Island to catch a glimpse of ponies roaming in the wild. I also enjoy a good sunset boat ride with Captain Barry’s Backbay Cruises or Spider’s Explorer.
What’s one thing that’s over-rated and can be skipped?
Skip Pony Penning. Yes, it’s what they are famous for, but EVERYONE knows it. It is basically a big stressed out mess here that week. If you want the experience, come a week or two before Pony Penning and check out the carnival to get the traditional Chincoteague feel without the lines, traffic, and inflated rates.
What’s the most under-rated activity you’d recommend?
I haven’t done this, but NASA does Astronomy Night at the beach like once a month, and it sounds pretty cool. They also hold events when there are meteor showers, and if you can swing being here for a launch, that’s definitely something you should see at least once. Another underrated activity is the Oyster Festival in October. People tend to go to the Seafood Festival in May over the Oyster Festival, but despite its name, the Oyster Festival tends to have a better array of seafood to choose from (I think that’s why fewer people go – they think it’s going to be all oysters). It’s worth checking out for all you can eat seafood and a pleasant atmosphere.
Is there any where off the Island that you recommend checking out?
Cape Charles, about an hour south of Chincoteague, is full of cute shops and historic homes. You should also check out Onancock (approx. 30 miles), a charming historical area with a lovely farmer’s market and some artisan stores.
I’m a lover of craft beer and wine. Are there any local breweries, wineries, or distilleries you’d recommend?
Black Narrows Brewing Co is the only spot located on Chincoteague Island, but there’s a handful of craft breweries and wineries within an hour or so of the Island. For your vino fix, Bordeleau Winery, Bloxom Winery, and Windmill Creek Vineyard are among my favorites. Bordeleau Winery is nestled along Wicomico Creek with plenty of outdoor space to enjoy their very reasonably priced wines. Windmill Creek is housed in an old historic home that you’re free to roam about (hello original hardwood floors!). Bloxom Winery has a bistro on Saturdays that is definitely worth checking out.
If an ice-cold brew is more your style, we’ve got Black Narrows on the Island, but there’s also 3 Knots Taphouse, Evolution Craft Brewing, and Burley Oak Brewing. 3 Knots Taphouse is located in Onancock and features up to 30 beers on tap, including some brews from Black Narrows Brewing. Evolution Craft Brewing is located in Salisbury and offers an extensive beer and food menu. Burley Oak uses a mix of new and traditional brewing methods to produce its beers in Berlin, Maryland.
How to see Chincoteague Ponies
I grew up hearing about wild Chincoteague ponies. Will I see them while I’m there?
Chances of spotting a wild pony are seriously high, and you don’t even have to be here during Pony Penning to do so! The best place for spotting wild ponies is on Assateague Island on the way to the beach. There’s a marsh area where they’re frequently seen, not too far past the park entrance. As you approach the beach, there is a fenced area used to keep ponies during medical checks (this is also visible from the road). If you’re visiting Chincoteague right after Pony Penning, check out the pins at the carnival grounds. And of course, there’s always the pony pin at the McDonalds right before you cross to Assateague Island (most McDonald’s have play areas, ours has ponies…).
Is there anywhere I can ride horses?
Queen Hive Farms is about 10 minutes from Chincoteague Island and offers guided trail rides. One of the trail horses is a former Salt Water Cowboy (the horses used to round up the wild ponies for the pony swim during Pony Penning). This is also the farm where most people send the ponies they purchased through auction until they make other arrangements, so there’s a slight chance you’ll see a wild one while you’re there (sorry, no riding these). For horse owners out there, they also offer vacation boarding for those interested in bringing their horses to the beach.
A huge thank you to Allie for all the tips on things to do in Chincoteague and how to embrace the local vibe while on the Island! As someone who’s made several trips to Chincoteague Island, I am delighted to see some of my favorite spots mentioned, and can’t wait to check out the places I haven’t yet experienced. We’ll catch you around the island, Allie!
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