As we made our way across the causeway from the mainland and onto Chincoteague Island, we could sense that things were a little different, a little quieter, on this small, secluded island off Virginia’s Eastern Shore. The small maritime village of Chincoteague has a distinct charm that hearkens to earlier times, when life seemed a little simpler and less chaotic. The 1945 movie theater, The Roxy, is a perfect example of the nostalgia that permeates this unique island.

The Saltwater Cowboys

Despite Chincoteague’s secluded location and quiet atmosphere, one island tradition has become world famous and attracts tens of thousands of visitors. The Pony Penning and Carnival, now in its 87^th year, is held every year during the last week of July. Members of the Chincoteague Volunteer Fire Company round up the wild ponies on Assateague Island, pen them in a corral until the following day, and then, during “slack tide,” herd them across Assateague Channel to Chincoteague.

These “Saltwater Cowboys” then walk the ponies to the carnival grounds where an auction is conducted the following day for the herd’s foals. Proceeds from the auction and carnival support the volunteer fire department and, even more importantly, help maintain the health of the pony herd.

This cherished annual spectacle is extremely popular, attracting upwards of 30,000 visitors to view the swim. But visitors to Chincoteague don’t have to battle the crowds to see the wild ponies. These romantic symbols of freedom, whose numbers are decreasing in North America, can be seen from various spots in the Chincoteague National Wildlife Refuge. We viewed the ponies while riding bikes, while enjoying an evening scenic nature pontoon-boat tour, and while on the Refuge Wildlife Tour, a very informative tour sponsored by the Chincoteague History Association. This bus tour takes visitors to a private part of the refuge and is perfect for those who would find hiking or biking trails too much for them.

Although the ponies were quite a distance off, we also spotted two groups of them from the top of the Assateague Lighthouse. For a small fee, which goes to the fund drive to help fully restore the lighthouse, visitors can climb the steps of the lighthouse for some spectacular views of the beach, marshlands, and surrounding islands.

The Mystique of Misty

Chincoteague’s wide-spread reputation for its pony swim is due much in part to author Marguerite Henry’s 1947 children’s classic Misty of Chincoteague. This beloved classic was later made into a popular movie, which was filmed on Chincoteague using many of the local residents. Many sites from the book and seen in the movie still exist, such as Miss Molly’s Inn on Main St. and the Island Roxy, where the real Misty once strolled the aisles. Her hoof prints are memorialized under the old movie house marquee.

Misty herself, as well as her foal Stormy, who later got her own story book, are preserved and on display at the Museum of Chincoteague Island. The museum, which is dedicated to the celebration and preservation of the history and traditions of Chincoteague and its people, has a number of interesting artifacts and exhibits celebrating the island’s culture and heritage.

“America’s Best Beach Town”

Chincoteague’s ponies are a major attraction, but the town didn’t earn a reputation as “America’s Best Beach Town” (as voted on AOL Travel) without more attractions than the ponies. Assateague Island, which is connected to Chincoteague Island by a short bridge, is the site of the Assateague National Seashore and the Chincoteague National Wildlife Refuge. The island and its pristine beaches are protected land, offering visitors unspoiled natural habitats for swimming, surf fishing, kayak tours, eco-tours, bird watching, and biking. The Wildlife Refuge has over 14,000 acres of beach, dunes, marsh and maritime forest and is a safe haven for more than 320 species of birds.

We rented bikes from The Bike Depot & Beach Outfitters, which is located just a few minutes by bike to the Wildlife Refuge and the beach. The Depot has everything you need for a family bike excursion or a trip to the beach. Bikes are great way to view some of the plentiful wildlife in the refuge including the ponies.

Another great way to experience the beauty of Assateague and view the abundant wildlife is by boat. Scenic nature tours and sunset tours are offered by a number of companies on Chincoteague. We enjoyed a very scenic and informative cruise with Daisey’s Dockside Nature Cruises, spotting dolphin, bald eagle, a number of aquatic birds, and, of course, some close-up views of the ponies.

Even before Chincoteague was known for its ponies, the island was known for its great fishing. Whether it’s the thrills of deep-sea sport fishing, or surf or channel fishing, or simply relaxing on a dock or pier, Chincoteague boasts a reputation as one of the premier fishing locations in the Mid-Atlantic.

Great Dining and Shopping

Downtown Chincoteague is small, but quaint and pedestrian-friendly. A nice collection of shops and galleries offers good shopping opportunities. Authentic decoys are a Chincoteague specialty, with downtown shops featuring them.

Dining in Chincoteague can be a real treat, especially for seafood lovers. With a diverse selection of restaurants to choose from, diners can feast on some outstanding seafood, whether on white tablecloths or waterside picnic tables.

While on Main St. we would recommend Bill’s Prime Seafood & Steaks for something a little more upscale. Bill’s has been a popular spot in historic downtown since 1960, serving great seafood, hand-cut steaks, and pasta dishes in a casual/elegant atmosphere.

Etta’s Channel Side Restaurant, located on the water on East Side Dr., also serves great seafood – we were quite impressed with the crab cakes. Chef/owner Janet Gadow has been meticulously preparing her fresh seafood for more than 15 years. The dining room is bright and cheery with wonderful views of Assateague Channel and the Lighthouse.

For a considerably more casual, yet equally rewarding, dining experience we recommend a meal at Woody’s Beach Barbeque. Serving some of the best BBQ ribs and pulled pork that we have tasted, Woody’s is a bit of a quirky dining experience, which is just what owner Larry Parsons strives for. Woody’s playground/eating area has a collection of funky decorations and artifacts, making for a dining experience equal parts delicious and fun.

Wide Variety of Accommodations

No matter what type of accommodations you prefer, you will find it in Chincoteague.
We enjoyed wonderful views of Chincoteague Bay from our room and private waterfront deck at the Island Resort. Rooms are newly renovated, large and quite comfortable. Amenities include indoor and outdoor pools, well-equipped fitness center (overlooking the bay), indoor hot tub with panoramic views of the bay, complimentary continental breakfast, and a 600-foot waterfront boardwalk with a variety of spots to sit and take in great views of the passing boats and glorious sunsets.

Visit the Chincoteague Chamber of Commerce website for information on activities, special events, dining, accommodations and more.

Getting Off the Island

Although there is a lot to do on Chincoteague and Assateague, travelers will find an interesting collection of maritime towns along Virginia’s Eastern Shore. We experienced a great kayak trip to one of the Eastern Shore’s wineries with Southeast Expeditions. Our guide, Margaret, shared a wealth of information about the Eastern Shore and its shell fishing industry as we paddled our way to Chatham Vineyards. We then enjoyed some samples of Chatham’s excellent wines while getting a tour of the winery’s production facility and some family history of the vineyard’s owners, the Wehners.

Southeast Expeditions has four locations and offers kayak trips for all levels of experience. Southeast’s kayak tours can help you explore the natural beauty of the Eastern Shore’s salt marshes, barrier islands, bays and even the ponies of Chincoteague.

After our kayaking excursion we proceeded to the intriguing town of Cape Charles. Located at the southern tip of the peninsula, Cape Charles is in the midst of a wonderful regeneration of its past glory. Its prominence as the gateway city for ferries from the Eastern Shore to the Virginia Beach area was lost upon the completion of the Chesapeake Bay Bridge-Tunnel.

Cape Charles has some wonderful beaches, interesting shops, and enticing restaurants, as well as some fabulous accommodations. We spent a night at the Hotel Cape Charles and were delighted with this completely renovated, chic, boutique hotel located on the town’s main business street and within easy walking distance to the beaches, town harbor, and shops and galleries on Mason Avenue.

During our stay in Cape Charles, we spent an enjoyable evening with Captain Dave and his mate Hania aboard the Stewardship on a two-hour sunset cruise. An excursion with Sail Cape Charles is a great way to enjoy the peaceful beauty of Chesapeake Bay and the shoreline of lower Eastern Shore.

Cape Charles is also home to the Bay Creek Resort and Club, a golf and marina community offering world class amenities, restaurants, and two outstanding golf courses. Vacation rentals are available.

Virginia’s Eastern Shore has a number of state parks, museums, wildlife refuges, and many other places of interest. Be sure to check the Eastern Shore of Virginia’s website for a wealth of information about things to do and places to see.

All photos by Ron Wrucke