Chincoteague on the Eastern Shore of Virginia

I have a great job that sends me to places that many people go to vacation. I’m lucky that I have both sides of the coin – great career and amazing travel. I’ve been to Chincoteague for work multiple times over the past year and a half, but July 2020 was the first time I was able to travel here during the high season, and to really see this little town abuzz! Of course, this is also in the summer of social distancing, so what I saw isn’t necessarily what things have always been like, or what they will be like in the future.

I tend to write my blogs as a chronological story, but since this is an amalgamation of trips, I’ll do a slightly different format.

If you come in the warmer months – BRING BUG SPRAY.

What to do?

Chincoteague and the neighboring Assateague Islands are barrier islands on the Eastern Shore of Virginia near the Maryland border, but not much else. Asssateague (twelve year old giggling) is a National Park/National Seashore/State Park/wildlife refuge and is mostly uninhabited. There are two ways to get there – through the Maryland side or through Chincoteague. It’s all really small, and if you’re not from the nearby area, this probably isn’t on your bucket list to visit. Unless you read Misty of Chicoteague as a kid and are super into horses.

Misty of Chincoteague by Marguerite Henry – Photo from Amazon

The Ponies

I read the book as a kid, and my mom swears I loved it. I recognize the cover, but I bought it again to refresh myself after this trip. There is a large herd/multiple herds of wild ponies on Assateague, which is really what makes the area famous. And the event to end all events is the annual Pony Swim in late July. Tens of thousands of people flock to the area to see the Salt Water Cowboys herd up the ponies and they swim from Assateague to Chincoteague. They’re checked out by a vet, and some of the foals of a certain age are auctioned off. This is for population control measures and all money, as I understand it, benefits the fire department which wouldn’t exist otherwise. I have never been and apparently it’s a HUGE deal and very exciting. If you want to go, you need to book your accommodations months in advance.

I wish the baby lying in between the ponies would have popped his or her head up for a better photo!

I wanted to see the ponies that I’ve heard about so many times, so I booked a tour with Daisey’s Island Cruises and loved the opportunity to check them out! My top three things I like to do on vacation are boats, books, and beer so this was awesome for me! We were on a pontoon boat with six people, a dog, and our captain, in the open air – so we had the chance to be physically distant and safe. He gave us a lot of history of the area and of the ponies. Here are my tips for your cruise:

  • Sunset cruise was perfect! Glad that was the one my coworker and I picked, it was lovely!
  • Bring cash to tip your driver!
  • BYOB! Would have been a little more fun with a beer or a glass of wine.
  • There are no bathrooms on the smaller boats.
  • Check the launch schedule at NASA Wallops – Daisey’s offers launch viewing too!
Boat rides are a great way to see the ponies!

Assateague Itself

As this is a park, there’s a fee to get in. But I got super lucky like I did with Joshua Tree and they weren’t taking money to minimize contact and the spread of the coronavirus. Therefore my entrance was free! I believe that if you ride a bike over, you don’t have to pay, but I’d maybe double check that one.

I only went to the beach to sit and read my book for awhile. I went to a spot recommended by a friend/local because he said there were cats there. (No cats were spotted!) It was about a half mile walk to the beach, so pick your beach spot carefully if you’re coming with kiddos and lots of gear. There was a pit toilet nearby, so that’s a bonus.

Assateague lighthouse

There’s more to do here than just the beach – there’s camping and a lighthouse and lots of hiking and walking trails. There’s a cool lighthouse too! You can get an (expensive) permit to drive on the beach itself, but there’s no road that goes from the Virginia side to the Maryland side – keep that in mind.

Space Nerdiness!

I am a huge proponent of space tourism. (Check out my tips for the Florida Space Coast!) If your kids are going to get the chance to eat ice cream and play on the beach, you gotta shoe horn some awesome aerospace knowlege into their brains. Ok, but moreso because I really love nerding out over rockets and space.

I have not yet stopped at the NASA Wallops visitor center – it was the #1 thing on my to-do list for my free time with this trip. Unfortunately the coronavirus had other plans and shut it down… which for the record I think is dumb because there are a bunch of exhibits that are outside that they could keep open. If you’re curious about if there’s an upcoming launch to see from the area, check out for the schedule of all the rockets going from all the ranges. (Just search for “Wallops”).


Being on the seashore means there were lots of different ways to get out on the water. There were lots of boats and fisherman and kayakers that I spotted. Because I drove by the sign every day on my way to work, I opted to go Stand Up Paddleboarding (or SUPing) on my day off. I was trying to be easy and go where I could walk and explore the area in front of my hotel – so I put in off Main St with the dude’s assistance; even though he said he could drive me somewhere else that was calmer and more popular with SUPers. (Also didn’t want to drive with someone because of COVID). It was fine, but the current was a little strong and boats kept going by and I could have made it easier on myself. Great workout though, highly recommend SUPing if you haven’t had a chance to try!

SUP brah?

Misc and things I didn’t do that seemed popular!

There are lots of places for tourist shopping on the island – get your cheezy shot glasses and neon t-shirts!

There are some oversized Adiorondack chairs that spell out LOVE at Waterfront Park on Main Street. Awesome stop for a photo op!

Love Chincoteague Island!

I didn’t partake, but there are several places along Maddox that were advertising fun golf cart and buggy rentals. Would be a fun thing to do if you’re going there with the family! Maddox is actually the fun drag where we saw some great cruising – I even saw a redneck hottub rolling down the road. It was a bunch of dudes in the back of a pickup truck with a tarp and a lot of water – it was hilarious!

Where to stay?

If you’ve read my Travel Tips – you know that especailly when I’m staying somewhere for business I always pick a place that’s going to get me free vacations later. For me that’s picking a Marriott, so while I’m here I’ve always stayed at the Fairfield Inn. It has an amazing water view, free breakfast, and is walking distance to several restaurants. I was also very impressed with how everyone was handling the coronavirus there and I felt very safe.

Definitely splurge for a balcony room at the Fairfield

Maddox Blvd is the main drag of the town – if you want to be close to more things, you can look for accommodations along here. But you may not find a lot that’s water facing. There are several campsites that were popular for the summer as well!

What to eat/drink?

Thanks to COVID-19, I’ve been used to calling places or stalking their social media in advance to see if they’re open. The same is true for Chincoteague Island – most restaurants are seasonal or have seasonal hours, so check ahead! Nothing is open very late here – I’ve gotten to my hotel after 9pm ready for dinner and my only option was to get a TV meal from the hotel store. Plan to eat a little earlier.

Pico Taqueria is the best!
  • I grew up in San Diego, so believe me that I am serious about my tacos. The best (American) tacos I have had outside of San Diego are amazingly on this island. Please make Pico’s your #1 priority. It might sound weird but the cauliflower taco was the best thing I had. They have a lot of options with local flavor too, and good craft beers. Cute branding and outside seating, definitely a line that shows you it’s worth it. You can try to call your order in, but if they’re too busy they won’t answer. (Seasonal)
  • My second favorite restaurant was Better – and it’s a food truck with picnic tables! Menu is always changing, and rumor has it the chef always goes to Virginia Beach to buy the best ingredients. DEFINITELY get the potato rocket and I loooved their brussel sprouts! (Seasonal)
  • Bill’s Prime is the fancy restaurant on the island, and they have great steaks and incredible seafood – go here if you like oysters. Good wine and fancy martinis. I’ve only been for dinner, but I heard their brunch and lunch are great too.
  • Ropewalk is great because it shares a parking lot with my hotel. It’s good American Food and has a fun bar. I like their portabello tacos.
  • Drink Tip: Be sure to try a Crush! It’s like a sparkling screwdriver, and a little sweeter. It’s the thing the island is known for!
  • Sometimes if you need to eat later, you only have Don’s Seafood as an option. I eat little to no seafood, and my coworker is a vegan, so we had a hard time finding options here, and they weren’t healthy. (Especially with the salad bar closed due to the virus). I really enjoyed their spinach and artichoke dip.
    • Upstairs is Chattie’s bar. Fun times!
  • Chincotiki is at the corner of Main and Church Streets with an amazing view of the water. Great drinks and average burgers. Love the outside setting, but definitely don’t come and freeze here in the off season! (Seasonal)
  • Poseidon’s Pantry was a great quick lunch stop for me in one of my off-season trips. Nicer fare, and a cute shop!
  • If you want the best beer on the island – go to Black Narrows! I have tried everything that’s been up for offer here and liked it all!
    • If you want to pick up great beer, go to the Thirsty Mosquito by the traffic circle. They have a lot of great craft beer and a good selection of everything else. I like the stuff from Rocket Frog Brewing – there’s a fun local connection to how they got their name, so look it up!

Places I didn’t visit but heard good things about:

  • Cosa Pizza is a trailer, but the locals all say it’s the best pizza on island.
  • Since I was already eating unhealthy by not being able to cook for myself, I deprived myself of desert. There are two places with huge lines and amazing reputations on Maddox Blvd – Mr Whippy and Island Creamery. I’d love to know if you try both and which you think is better!
  • Steamers – the locals drink here!
  • Sandy’s Pony Donuts – a local institution and they have a wall with wings painted on them for all your Instagram needs!

Getting there

Not to make you claustrophobic or anything, but there’s only one way to get to and from Chincoteague Island – and that’s via Chincoteague Road over a drawbridge. There are two main roads and if you give directions like “it’s on the roundabout” people will know the only location you’re talking about. It’s located on the “Delmarva” penninsula – so named because Delaware, Maryland, and Virginia all have their flags planted here. There is no good commercial airport, you’re going to have to rent a car if you’re coming from out of the area.

I have flown into Norfolk (ORF), which is Virginia Beach adjacent, into a DC-area airport, and into Philly. Shortest drive is the 2 hours from ORF. From any of the three locations, the drive is easy, traffic wise, but boring and full of cops setting speed traps in the little towns.

Side trips

I did have some free time due to a trapped weekend on my last business trip here. I took a detour to Virginia Beach because my best friend lives there now. I’ve stopped by her parents house on my way to/from Chincoteague on all my past trips. Obviously a great place to visit the beach, which you can tell by the name. I’ve also stopped by the boardwalk to see the Triton statue that I’ve seen in so many of my best friend’s photos. I don’t have any tips on where to stay or what to eat because I’m always hanging at my friends house, but know that it’s about two hours south.

Per my previous comment about looking for boats, beer, and books, on my first trip to the area in 2018 I took a detour to visit Dogfish Head in Delaware. Amazing beer, and I actually really loved the restaurant too. They have a cool outdoor area and a great shop. I was hoping on my most recent trip that I had a half day coming to me that I could make a run up there, but that didn’t materialize, and they only had curbside pickup anyway. Maybe the only thing I’d actually want to do in Delaware – I stopped for the beer so I could count this as a state I visited.

A note about Coronavirus Travel

As I finish writing this post in early August 2020, I can reflect back on how things have changed since we first heard about the virus and since California went into isolation in March. When you read these words I don’t know what the world will look like, because all I know is the rate of change of things is incredibly fast.

My most recent trip to Chincoteague was absolutely essential. If you’re local to the area and can come, I think that would be a great thing, but I wouldn’t fly anywhere right now. The airlines are giving a lot of lip service to their HEPA filters and cleaning procedures, and the airports are similarly putting stickers on the floor and closing things down. But the truth is that there are a lot of people that simply care more for themselves than their fellow humans and are either willfully disobeying the mandates, or are just lazy about masks. This puts you at risk, and it’s exhausting for both the airlines, airports, and you yourself to continue to fight with the Karens and the Kens of the world out there. I flew with an N95 mask that was provided by my company, and I wouldn’t fly without a mask like that that protects me. (Cloth and surgical masks are to protect others, N95s protect you – check out this video for info from someone smarter on it than me). Side note to add I believe the frontline workers need N95s more than average people, so I don’t use them up unless I’m in a difficult situation like flying.



  1. As always – so informative! Misty was on regular rotation in my books as a child! I only know of this island because of it – and now your great recommendation! I definitely want to visit!


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