Chincoteague narrowly missed nabbing the honors for America’s Coolest Small Town this year, placing 2nd in the national contest. Nonetheless, we still think Chincoteague is pretty cool in it’s own right. The island town packs historic charm, beach vibes, grand views of the bay and the ocean, and plenty of local flavor. We made the short trek south to the Eastern Shore of Virginia last Friday for a day of exploring, and while the wind and unseasonably cold temperatures were not in our favor, our spirits were not dampened.

First on our agenda was hitting the beach. Again it was cold and windy (really, REALLY windy) so the exploring was cut short, but not before we gleaned a little history. Being a stone’s throw from Assateague, we naturally find ourselves exploring the Assateague National Seashore more than the Chincoteague National Wildlife Refuge. The Wildlife Refuge was established in 1943 and includes more than 14,000 acres of beach, dunes, marsh and maritime forest. The natural beauty is awe-inspiring, which is probably why it consistently ranks as one of the most visited refuges in the United States. Starting May 1, refuge hours will be 5am until 10pm. Also on the horizon are International Migratory Bird Day (May 9) and the Sunrise Pony Walk (July 27). The pony walk is a major island event, with hundreds of onlookers pouring in to watch as the Saltwater Cowboys move a large group of Chincoteague ponies from the northern section of the refuge down the beach to a corral in preparation for the Annual Pony Swim.

Speaking of ponies, in case you’ve majorly, majorly missed it, much of Chincoteague’s notoriety comes from the famed book (and later movie), Misty of Chincoteague. Of course Misty is honored throughout the town, with statues, books, and namesakes prevalent along Main Street.

Beyond the draw of the famous beaches and ponies is the small town charm. An eclectic mix of retail shops and art galleries is interspersed with dining options from sweet smelling bakeries to (our favorite part of course) seafood-heavy restaurants like Don’s Seafood Restaurant or Bill’s Prime Seafood and Steak. A trip to the beach, a stroll along Main Street, and Stops in Wine Cheese & More (home of the Chincoteague Wild Pony Wine), Egret Moon Artworks, Howl Naturale, and Sundial Books had us feeling pretty hungry…and eager to check out the recently remodeled bay front restaurant, The Jackspot.

The Jackspot, located within convenient walking distance from the Fairfield Inn & Suites, boasts 180-degree views of the Chincoteague Bay. Fresh seafood and tropical libations are obvious options here, as are sunset views from the tropical beach or inside in the Narrows Ballroom. Of course we couldn’t resist noshing on some seafood, immediately ordering the fried calamari & pineapple and the crab & avocado salad. We’ll let the pictures speak for themselves…

With summer just around the corner, the busy season is coming in strong in Chincoteague, with events like the Annual Pony Penning, the Chincoteague Blueberry Festival and the 90th Annual Firemen’s Carnival all on the horizon. Take a trip to Chincoteague and enjoy the dining, shopping, and beaches all summer long. We’ll be back soon!

Until next time…