Chincoteague: Where Wild Ponies LOVE to Swim

On the northern side of VA US-13, when I turn next to a local’s favorite landmark, I find myself headed to the most eastern point of Virginia. It’s a peaceful drive, which includes a 4-mile causeway that carries me off the mainland of the Eastern Shore. When I arrive, I encounter an island beach town that feels as if it’s been cocooned from time. And as I turn to my family in the car, I wonder why it has taken me so long to visit here. Because I know immediately that this place is going to create some new favorite places, and some new cherished memories for the years to come.

Chincoteague is an island town,  located about a 4-hour drive east of Richmond. Its unique name is Native American derived (Gingoteague) and a common story says that it means “Beautiful land across the water“. 

What the island is likely most famous for is the annual Pony Penning. During this event, the wild ponies are herded by the “Saltwater Cowboys” from Assateague Island to Chincoteague, where the fouls are auctioned off. This year marked its 100th anniversary – And thanks to Marguerite Henry, this event will forever be remembered through her children’s book Misty of Chincoteague.

There is one official LOVE sign in Chincoteague’s downtown off of Main Street. You’ll find another not too far away on Rt 13 at the Welcome Center of New Church. Our family decided to take our summer beach vacation here (so there’s a lot to write about :). And as you may know from previous blogs, the Eastern Shore is where I grew up (for me, about an hour south of Chincoteague). So it’s always special to write about places here.

Since we spent a whole week here, and I try to keep these reads less than 10-minutes, I’m going to bucket our experiences into three categories: (1) Where we shopped, (2), Where we ate, and (3) What we did

Where We Shopped

While Chincoteague has been a beach town for some time, it still has that small-town feel. Which is what we experienced in many of the locally owned shops in the area. Some of the ones we went in include (in no particular order):

• Island Time Resort Wear – here you’ll find all of your beach accessories, clothing and gift items to remember your trip. We bought some fun Chincoteague swag to wear at home
• Sundial Books – you’ll find a nice selection of new and used books across various genres. We found a “Boxer’s for Dummies” book that made us laugh
• Island Artisans – a very quaint shop that also features locally made gifts and my favorite, Chincoteague’s LOVE sign ornaments.
• The Osprey Nest Art Gallery – a beautiful selection of artwork by renown wildlife artist Kevin McBride (who also creates the annual pony penning poster) and gift shop with unique finds also created by local artists
• Hollyhocks Home Decor – a lovely boutique that sells “ethically sourced, Fair Trade, unique and quirky items”. Here, you’ll also see an unofficial LOVE sign in the store

Where We Ate

Keeping with the local theme, you will find very few “chain-type” restaurants. Here, you have numerous options to satisfy even the pickiest eater. And of course, it’s some of the freshest seafood you can eat. A few of the places that we enjoyed included (listed at random):

• Main Street Shop and Coffeehouse – just as the name says, you can get a cup of Jo, and do some shopping while you sip. In addition to coffee, they serve fresh pastries and pitaya bowls (a type of smoothie bowl made from blended dragon fruit)
• Famous Pizza and Sub Shop – when we knew we’d be at the beach all day, we came here to grab delicious sandwiches for an easy lunch. The portions are huge and they are great leftovers as well 
• Island Creamery – not sure you can say you’ve been to Chincoteague if you haven’t had ice cream here. It’s all homemade and the selection of flavors is amazing. Every bite is worth every calorie consumed (LOL)
• Blackfin Island Grill and Tapas Lounge – their website said it best “Where local meets a little unexpected”. Our family enjoyed fried clam strips, a tuna poke bowl, and prime rib (our oldest said it was the best)
• Bill’s Prime Seafood and Steak – here you’ll find tablecloth service with a casual ambiance. Serving the area for over 60-years, you will not be disappointed by anything you order off the menu. It’s also a wonderful place for a date-night
• Gary Howard Seafood – if you’re looking to enjoy fresh seafood where you’re staying, this is the place to go. We enjoyed steaming fresh crab legs, shrimp and clams at the home we were renting
• AJ’s on the Creek – we loved this place so much, we ate here twice. The cocktails were delicious (the key-lime pie martini was to die for) and the Oysters Romanoff were the best I’d ever had. They’re freshly made breakfast, lunch and dinner menu options are definitely worth the wait

And finally, Extra Sweets – a classmate of mine started a small baking business where you can call ahead and order several different types of homemade baked goods. The Pecan Sticky Rolls and Cinnamon Rolls tasted like heaven in our mouths.

What We Did

There are certain activities one might expect in typical beach towns. Chincoteague has those and also some of the unexpected for visitors to enjoy. Here are some of the things we got to experience while in the area:

• Lounged on Assateague Island Beach – I get that I’m biased about the Eastern Shore of Virginia, but there is no other beach like this place. Great waves from the Atlantic Ocean and you are almost guaranteed to see the wild ponies as you drive to the island. There are also multiple trails available to escape even further into nature (bring bug spray)
• Played 36 holes Surfside Golf – it’s hard to imagine a beach trip without a round of putt putt. We enjoyed the first 18 holes so much, we stayed and finished out the other 18-holes before leaving (one is less challenging than the other)
• Visited the Museum of Chincoteague Island – this is a great way to learn about the area’s history and what makes this place so special
• Went shark fishing with Fish Tales – this establishment offers numerous fishing adventures so you can tailor to your angling needs. And while we didn’t catch the big one this time (the nor’easter made it impossible) our guide still made the trip on the skiff a lot of fun
• Walked to the Assateague Lighthouse – a short stroll will take you to this mid-1800s built lighthouse. The red and white stripes also make it a tried-and-true lightship along Virginia’s coast. And while the walk is easy, I recommend you bring bug spray, and consider long sleeve clothing. This was one of the only spots on this trip where the mosquitoes were an issue
• Grabbed drinks on the bay – there is nothing better than enjoying a beverage while sitting next to the water. We found these places at Ropewalk Chincoteague, and Don’s Daughter – both overlooking the Chincoteague Bay with nice views of the sunset

Chincoteague is a place to love…

For as long as I lived on the Eastern Shore, I had never vacationed on Chincoteague before. And now that I have, I can’t believe it took me this long to stay there. What a hidden jewel this place is. It provides its visitors with traditional coastal-town feelings, without the overwhelm of a big touristy beach area. It’s where nature, history, sand and sun come together to create a setting like no other. If you love the beach and are looking for something a little outside the box, Chincoteague could be the seaside getaway that you’re looking for.

Want to see where the wild ponies swim? Then gallop on over to their chamber’s site.

♥️♥️♥️♥️

Official ♥️ Signs Visited      =     64	LOVEworks Official Signs  =  336
Unofficial ♥️ Signs Visited  =    55	LOVEworks Unofficial Signs = 400+
TOTAL VISITED    =     119	TOTAL LOVEworks Signs      =  700+

Is this your first Leah LOVES Virginia blog post read? Thank you for taking the time to visit. If you’re wondering how this adventure got started, check-out my first blog post and my about page. Want to stay connected? It’s super easy and you’ll only hear from me when a new blog gets posted. You can also follow along by friending me on my Leah LOVES Virginia Facebook page.

Important note: I always do my best to ensure everything in my blogs are factual and that I give credit and use quotations when pulling information from sources. If you believe there is something here that needs to be addressed, please email me directly as I want to be sure it is fixed. Thank you and happy LOVE sign hunting.