How would you describe Virginia’s Eastern Shore? If you’re like me, the southern side of the Delmarva Peninsula conjures up long stretches of highway punctuated by crepe myrtles and tomato stands, ramshackle buildings that look as if the next Nor’easter will blow them away, and nondescript shopping centers with a fast food joint or two. That’s about it, right?

I used to think so. In fact, for the past ten years, I’ve visited the Shore twice each summer to drop off or fetch my sons at the Y’s Camp Silver Beach. My husband and I would cross the tunnel, pedal to the metal, power up to Exmore, turn around, and dash back home with nary a glance to the left or the right. The occasional trips up north to Philly and beyond? It was always: How fast can we drive along Route 13 without risking a speeding ticket? It was never: Let’s stop and explore what lies off the highway.

Well, I have news for you. A whole world awaits just around the bend on Virginia’s Eastern Shore: quaint towns with boutique hotels, chic restaurants, and wine bars; waterfront homes with stunning views of creeks and rivers; a fishing industry that dates back several centuries; artists whose creativity knows no bounds; and honest, hardworking people who love the Shore’s natural beauty and peaceful vibe.

Who knew?

My college friend, Robin, and I spent four days exploring the Shore in September and decided the peninsula across the water deserves a better reputation. The truth is we have a playground in our backyard most of us don’t even know about. Sure, there’s a bridge-tunnel in the way and a toll that seems a little steep. But it’s a small price to pay considering our proximity to some of the prettiest parts of Virginia. All you have to do is slow down and look.

A SWIRL OF COLORS

Who hasn’t heard of Misty of Chincoteague? Most women I know grew up on horse stories, fantasizing about being a cowgirl and owning a pony like Misty one day. The Pony Swim is a legendary event held each summer in Chincoteague (that’s “Shink-a-teague”), and while our visit didn’t coincide with the swim, Robin and I learned all about it from Captain Dan, whose Around the Island Tours are an excellent way to see the barrier islands from the water and learn about the history and culture of the region.

Captain Dan, who’s from Chincoteague, filled us in on what it’s like to grow up in such a small community. Only 4800 people live on the island, and in the winter the population drops to 2000. “It’s a really nice place to raise your family,” Dan said. On the tour, he showed us where the ponies swim from Assateague Island to Chincoteague each July during the Pony Round-up. Run by the Chincoteague Fire Department, the event serves two purposes: it keeps the wild herd from growing too large and helps fund the fire department. More than 40,000 folks attend the event yearly, a few of whom will head home with a new pony as a souvenir.

As Dan continued circling Chincoteague, he showed us a small group of wild ponies grazing on Assateague Island. Later we saw a pregnant mare that looked like she was ready to pop. Dan also pointed out two bald eagles, as well as egrets, great blue herons, and shorebirds. The two-hour tour highlights much of what makes Chincoteague special.

In fact, I was surprised to find how much this cute little tourist town has to offer. In the Chincoteague National Wildlife Refuge, for example, you can hike and bike on lush wooded trails and then swim and stroll on an amazing beach with fine white sand and shells aplenty. At sunset we saw families gathered for evening cookouts, their fire pits blazing and marshmallows at the ready. As the sun set behind us in Tom’s Cove, Robin and I walked along the beach, dipping our toes in the Atlantic. Above us the sky swirled with colors, and everything glowed pink and gold.

TRADITIONAL LIFESTYLE

During the night a front moved in, so Robin and I awoke to low-hanging rain clouds, worried that our trip to Tangier Island might have to be canceled. Luckily, as we pulled into Onancock, the rain clouds lifted, and we joined three other women on the Joyce Marie II for the 60-minute ferry ride to this isolated island in the middle of the Chesapeake Bay, known for its crab and fishing industry, as well as its unique personality.

Upon arrival, Robin and I were met by Michelle, a Tangier Island resident who offers island tours on her golf cart, the preferred mode of transportation on the island. Weaving through narrow streets, Michelle shared the island’s history and culture. At three miles long and 1 ½ miles wide, “there’s no chance of you getting lost,” she said with a grin. And with a population of 500, “you can’t get away with anything here,” quipped Michelle, who loves living on the island and “would never live anywhere else.”

According to legend, Captain John Smith bought Tangier from the Native Americans for two overcoats. During its heyday, the island boasted 1200 residents, but a moratorium on crab licenses is preventing a new generation of watermen from making a living, forcing many of the youth off the island to find work.
Denny Crockett, who gave Robin and me a tour around Tangier on his boat, said, “We talk about saving the bay. We talk about saving the crabs. We need to talk about saving the watermen.” Indeed, it’s the hardy, independent nature of these hardworking individuals that has made Tangier the unique place that it is—and supplied our tables with delicious Chesapeake Bay seafood for centuries. Denny insists the watermen understand the cyclical nature of the fisheries and would never deplete the crab or oyster populations. It is their livelihood, after all. To learn more about the watermen and life on the island, stop by the Tangier History Museum, where you can see videos with interviews of local residents and displays of Tangier Island’s interesting past.

As we chugged around the harbor, I made a note of the poetic names in faded paint on the sterns of the fishing boats—“our wives and daughters,” said Denny—Sandra Gail, Joan Marie, Elizabeth Joy, Claudine Sue, Amber Leigh, Valerie Faith, and Betty Jean. While visiting a crab shanty, where watermen oversee the shedding process that produces soft shell crabs, I spied crab baskets marked with names of watermen—Eddie, James, Hoot, Wayne, Paul, Burke, Ron, and Mitch. Behind these names are a proud people, who cling to a traditional lifestyle in the face of modernity.

Back in Onancock, Robin and I visited a few shops in the cozy downtown area: Dawn, a trendy boutique that supports cottage industries both on the Shore and beyond; gardenART on King Street, a whimsical shop with garden supplies, art, and home décor; and Red Queen Gallery, where local artists display their talented wares from hand-wrought jewelry to fiber arts and everything in between. Both Robin and I were quite taken with Onancock, a quintessential small town. Its lovely location nestled next to a picturesque harbor, together with big-city amenities—classy restaurants, a wine bar, an independent movie theater, a playhouse offering year-round live theatre—attract a number of retirees and families seeking a more laid-back lifestyle. We also noted a sense of community spirit you won’t find in larger cities that added to Onancock’s appeal.

COOL BREEZES

The clouds departed on our third day on the Shore, revealing an azure blue sky—perfect weather for our winery kayak tour with Southeast Expeditions, a 12-year-old business owned by Dave Burden, a likeable fellow who’s passionate about preserving the Shore’s unspoiled beauty. We met Dave at the Machipongo Trading Company and followed him to a sweet little cove called Bayford, where a retired couple joined us. Our paddle took us up Church Creek, and after about an hour of leisurely paddling, we beached our kayaks at Chatham Farm, an elegant estate (circa 1818) and working farm that produces a variety of crops, including 20 acres of vinifera vines, whose grapes are transformed into French-style wines under the Church Creek label.

Jon Wehner, a second-generation winegrower, took time from his busy harvest season to welcome us and show us around the winery. We watched as just-picked grapes were pressed into purplish-blue juice that snaked through a clear pipe to a tall steel vat, where the first stages of fermentation would begin. I spied a recliner in a corner of the barn, and Jon admitted that this time of year, he spends long hours tending his wines and catches a few much-needed winks whenever he can. Jon says the sandy, loamy soil and maritime climate on the Shore are perfect for making Bordeaux-style wine. Robin and I enjoyed tasting the fruits of Jon’s labor, especially the 2008 Vintner’s Blend and the 2009 Chardonnay, Oak Blend.

Next stop was Cape Charles, a darling town on the shores of the Chesapeake Bay, which Robin and I toured by bike as the afternoon sun set slowly in the western sky. The town is about seven blocks square and features a sandy beach at its western edge, a new park in the center, and a downtown area overlooking the harbor. To the north, where Bay Creek Resort’s busy marina flanks a small shopping area, vacation homes dot the landscape in bright pastels, providing a marked contrast to the Victorian homes in the town proper, whose wide verandas welcome cool breezes and encourage yoo-hoo’s with neighbors who stroll by in the evening.

A clear blue sky greeted Robin and me on our last morning on the Shore, and after breakfast, we headed to Triple M Ranch just a mile from town to join Leslie, the ranch’s owner, for a guided trail ride through pastoral landscape and old wood forests. Leslie, who moved to the Shore with her family from Virginia Beach, says it’s a fabulous place to live and showed us around her property, sharing her ideas for the future. While we walked most of the time, my horse, Trooper, sped up to what’s called a running walk on occasion, a gait that Leslie explained was favored by gentlemen farmers when surveying their large properties. In fact, the Shore’s agricultural roots hark back four centuries when colonists recognized the potential of the fertile farmlands on this quiet peninsula.

That’s what gives the Shore its charm, I think. It’s relatively untouched by the homogenous effects of progress and retains a unique vibe, reminiscent of days gone by. When people ask Dave Burden how far Cape Charles is from Virginia Beach, he replies, “Twenty dollars, twenty miles, and twenty years.” With a little luck, the Eastern Shore will stay that way for generations to come.

For more info., visit esvatourism.org.

WHERE TO EAT
Chincoteague
• Woody’s Beach BBQ – Gail, the owner, says it’s not just lunch, “It’s an experience.” Tiki huts, Bob Marley tunes, Hawaiian shirts hanging from clotheslines, crushed oyster shells underfoot, and superb BBQ redolent of wood smoke and spice combine to ensure that Woody’s is worth a return visit. woodysbeachbbq.com

• Don’s Seafood Restaurant – A fixture in downtown Chincoteague, Don’s promises traditional seafood fare and delivers tasty plates of stuffed flounder and fried oysters. If you’re in the mood to socialize, check out Chattie’s Lounge upstairs where the dance floor thrums with the latest sounds. donsseafood.com

Tangier
• Hilda Crockett’s Chesapeake House – Family-style meals served at large tables remind you of Grandma’s house and the food is just as good. Standouts included the crabcakes, which were two inches thick and quite simply the best I’ve ever had, and the clam fritters, crunchy bites of fried goodness. chesapeakehousetangier.com

Onancock
• Mallard’s at the Wharf – Home of Johnny Mo, the musical chef; an amazing BLT with smoked salmon and horseradish sauce; and seasonal dockside happy hours with live music. Ask for a tour of the historic building, which once served as a bank. mallardsllc.com

Machipongo
• The Machipongo Trading Company is a surprising treat along Route 13, the perfect stop for breakfast or lunch and a cup of locally crafted coffee, micro-roasted by Eastern Shore Coastal Roasting Co. Kristin, the owner, sells a variety of gourmet foods as well as sandwiches, wraps, salads, and “killer smoothies.” Don’t miss the wild sockeye salmon salad, homemade pimento cheese, and delicious berry iced tea. esvamtc.com

Cape Charles
• Cape Charles Coffee House – A cozy haven in downtown, this coffee shop features home-cooked breakfast and lunch and friendly service from the owners, Marshall and Roberta, transplants from Napa Valley who absolutely love living in Cape Charles. “It’s the people,” says Roberta, who makes delectable scones and insists on a hug when it’s time to go. capecharlescoffeehouse.com

• Aqua – This upscale restaurant near the Bay Creek Marina offers stunning views of the Chesapeake Bay and food to match. We loved the Thai Shrimp appetizer, which everyone we met recommended, and the she-crab soup, whose creamy base tasted like the sea. Another standout was the green tomato caprése salad. Yum. baycreekresort.com/dining/aqua.asp

Chesapeake Bay Bridge Tunnel
• Just opened, the Chesapeake Grille located next to the pier is well worth a stop. Its beautiful interior frames large picture windows revealing the majestic beauty of the Bay, a perfect setting to enjoy their signature fried flounder sandwich or smoky-sweet BBQ. cbbt.com/tour.html

WHERE TO STAY

• Chincoteague – The Island Motor Inn Resort, conveniently located downtown, faces the water and features resort amenities such as an exercise room and two pools, one inside and out. Robin and I loved unwinding by the pool and filling up on the fresh-cooked breakfast at the café. islandmotorinn.com
• Tangier – Experience a quieter way of life on Tangier Island. Hilda Crockett’s Chesapeake House B & B includes breakfast and dinner. chesapeakehousetangier.com

• Onancock – I wasn’t a B&B aficionado, but now I’ve seen the light—thanks to Kris and Lisa, owners of the Inn at Onancock. A meticulously restored Victorian, the inn features five rooms each with its own tasteful decor. Luxurious 1200-count sheets, jetted tubs, a “wine-down” social hour with extraordinary wines and cheeses, and an exquisite breakfast convinced me that staying in B&Bs is the bomb! And the Inn at Onancock is one of the best. innatonancock.com

• Cape Charles – Blue, a new boutique hotel downtown, offers loft accommodations with views of the harbor, a well-equipped kitchen, flat-screen TV, and mosaic wall art in the large marble-tiled shower. The building’s original elements, such as the wide-planked wooden floor and brick walls, gives the hotel a big-city feel. But you won’t hear a big-city racket in this small town, just the quiet chirping of crickets and the breeze off the Bay that rustles your curtains. Ask about the cool beach cruisers, free for guests to use. capecharlesblue.com

• Kiptopeke State Park – At the southern tip of the Eastern Shore, this park is among the smallest in the state, but hugely popular among fishermen, birdwatchers, and families who love the park’s peaceful vibe. Besides camping, large modern lodges that sleep 16 offer an excellent option for family reunions and are affordably priced. Plus there are cabins and even a yurt available for rent. A beautiful beach, nature trails, and boating opportunities combine to create an idyllic retreat practically in our backyard. dcr.virginia.gov/state_parks/kip.shtml

DIVERSIONS
• Around the Island Tours in Chincoteague - Visit captaindanstours.com.
• Trip to Tangier aboard the Joyce Marie II - Visit tangierferry.com.
• Shopping in Onancock - Visit onancock.org.
• Winery Kayak Tour - Visit southeastexpeditions.net.
• Chatham Vineyards - Visit chathamvineyards.net.
• Triple M Ranch - Call 757-695-1780 or email Leslie at This email address is being protected from spambots. You need JavaScript enabled to view it. .