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This is a free excerpt from my book, Eastern Shore Road Trips #2: 26 MORE One-Day Adventures on Delmarva. More info about that and my other books exploring the history, travel, and culture on the Eastern Shore and in Delaware here.

At the risk of going all Buddhist on you, here is a piece of advice when it comes to wandering the backroads of Virginia’s Eastern Shore: Stay in the moment. Travel guides like this tend to send you over to this town and down to that waterfront and across to a pretty park, so you end up traveling with a checklist of an itinerary.

Here in this oceanside ramble, for example, the first official item on the list is Wachapreague. I’m going to suggest taking a roundabout way there to demonstrate the mindful point at hand. Jump off the Route 13 highway at Accomac and find your way to Drummondtown Road. Turn south and you’ll be 10 winding miles from the storied “Little City by the Sea.” 

Perhaps you’ll have a podcast going. Maybe you’ll be gabbing with the spouse or friend in the passenger seat. That’s all well and good, until you zip through Locustville with thoughts elsewhere. It’s a classic blink-and-miss-it crossroads, a smattering of old houses with no shops or restaurants. But give the place a smidgeon of attention, and you’ll see that it has a time-capsule quality. The historian Kirk Mariner once described Locustville as the closest thing left to the way things looked on the Eastern Shore of Virginia before the Civil War. 

A legend hints at the kind of place this was back then—not rich or important, more like just another stagecoach stop. According to that tale, a Locustville man traveled to Baltimore in the early 1800s looking for a wife. When he found a woman to his liking, he wooed her with talk about his glorious “Southern plantation.” She married him up in the city. When she got here to Locustville and took a look at her new home, she had this to say: 

Southern plantation, humph! Shabby Hall! 

The name stuck. Everyone in town started calling that place “Shabby Hall.” It’s still standing, but not here, oddly enough—it was moved across the Chesapeake Bay a while back, to a spot outside of Prince Frederick, Md. By the way, that couple apparently lived happily ever after in Shabby Hall, ’til death did them part.

Keep an eye out for 28251 Drummondtown Rd. That building started life as a general store in 1844 and remained open into the 1990s. Two doors away, at 28269, is the former Locustville Hotel, which began serving stagecoach passengers in the 1820s. The Folk Victorian-style Locustville Academy at 28055 opened in 1859 as a sort of prep school, with girls studying downstairs and boys up on the second floor. 

Many smaller houses date from that period as well, so it won’t take much effort to block out the pavement and the electric lines, leaving a view straight out of the mid-1800s stagecoach days. So it goes along these Virginia backroads: Be on the lookout for sweet, off-the-checklist rewards.

Fishing for Stories in Wachapreague 

Fishing Fleet Wachapreague Virginia from Town of Wachapreague Website

A scene from Wachapreague

Five more winding miles on Drummondtown Road takes you into the “Little City by the Sea.” Head straight to the waterfront: In front of you is Wachapreague Channel, which heads into Finney Creek, which runs into the ocean. The barrier islands called Parramore and Cedar are in the distance, the former straight east and the latter up a bit to the north. 

White people didn’t arrive in Wachapreague until relatively late in the game, the mid-1700s. Even after that, the place was just a family farm for decades. The first business came along in 1788—a gristmill that ran its waterwheel not in the traditional way, via the current of a flowing stream, but by way of tidal flows that roll through here with uncommon speed and force. A shipping dock went up in the early 1800s. Shipyards popped up as the town took shape. Oyster-packing outfits thrived. 

Steamboats came along in time. There is a street today called Ice Plant Road, because that’s what used to be there. In 1881, a man named Alfred Kellam surveyed this working- class enclave—it was called Powellton then—and decided it would be a first-rate tourist attraction. He built a hotel and commenced advertising: Powellton as a sea side resort has many attractions for lovers of gunning and fishing. … Bathing unsurpassed a short distance of the hotel. 

The ads worked. Outdoorsmen started arriving from Baltimore, Philadelphia, and New York City. As the 20th century dawned, a man named Gordon Mears took that campaign to another level. He replaced Kellam’s hotel with a four-story, 30-room affair bedecked with expansive porches, stained-glass windows, and an elegant dining room. The opening-day gala at Hotel Wachapreague on Sept. 18, 1902 had guests riding boats out to Cedar Island, where a sumptuous meal was served on the beach. Actor Ronald Coleman and former President Herbert Hoover were among the many notable visitors in the years that followed.

The hotel burned in the 1970s—it used to be where the waterfront Island House restaurant stands nowadays. As you stroll up Main Street today and see only a couple of little stores, think about how the Little City by the Sea might have looked during the Roaring ’20s, when there were a dozen shops, as well as a movie theater and a pool hall. 

Every one of the old buildings in town must have stories to tell from those days. Consider one example: the Eva Stevens House at 17 Main St. Parts of the building date to the late 1800s. In one of those anomalies that pop up in small towns like this, there used to be a general store located in the backyard. During Prohibition times, the legendary Eastern Shore character Southey “Sud” Bell lived here. He had a secret compartment built under the kitchen floorboards, where he kept a whiskey barrel hooked up to a sink so that one tap poured water while the other released something a little stronger. 

Before coming to Wachapreague, Sud Bell earned a measure of fame as the last-ever full-time resident of nearby Hog Island—the guy who stayed after storms and eroding shorelines had driven everyone else onto the mainland. With the population down to one, Bell proudly, and loudly, proclaimed himself the “governor” of Hog Island.

Wachapreague Hotel

The old Wachapreague Hotel

He was also a musician. This description of his performance style comes from an old issue of a newsletter put out by the Barrier Islands Center museum:

This wonderfully outrageous entertainer with his trademark cigar would stroll into towns singing at the top of his voice. People could hear him coming 15 minutes ahead of his arrival because of the parade of children following him as he strummed his banjo and sang. Some swear that he could not finish a song without stopping to tell a joke or a story. Walter Chrysler and Governor Tuck of Virginia were among the prominent people who invited Bell to entertain in Richmond and New York. 

Alas, the decades that followed those glory days brought one bit of bad luck after another into Wachapreague. There was the Depression, of course. There was a hurricane in 1933, then a fire in 1935. The town took another hit when the infamous Ash Wednesday storm rolled through in the spring of 1962. But you will see evidence nowadays that the Little City by the Sea is still plugging along. A good number of outdoorsmen and women still visit for the fishing and the hunting. There are bait shops, boat rentals, and charter vessels. The carnival grounds spring into action come summertime, thanks to a local fire company that’s been running those rides since the 1950s. 

Fishing Villages and Island Views

As Main Street heads out of town, its name changes to Wachapreague Road. Don’t go all the way back to the big highway. Turn left at Seaside Road instead. That will put you southbound on a two-lane road that runs 50 or so miles down to the bottom of the peninsula. Food and restrooms will be in short supply, but the highway will always be a quick detour away. 

View of Broadwater, Virginia from top of Hog Island Lighthouse

A view of Broadwater, Virginia from the top of Hog Island Light in about 1930.

The route number on Seaside Road changes from 605 to 600 as you cross a couple of little waterways, the Machipongo River and Frogstool Branch. Take Quinby Bridge Road (Route 182) ast over a channel to enter the first of the three sweet oceanside fishing villages on our checklist. Quinby dates its history to the late 1800s when a bridge first went up over that channel, making it easier for watermen and seafood processors to get goods to the then-new railroad line in the middle of the peninsula.

The main part of town lies along Upshur Neck Road. Turn left at Harbor Drive to find your way to a marina set on Upshur Bay. Parramore Island is out in that pretty distance again. Stick with Upshur Neck beyond town, all the way to a dead end, so as to savor all the waterfront scenery Quinby has to offer. Headed back down Seaside Drive, the next fishing village on the list is Willis Wharf, which you can reach by turning east on Willis Wharf Road, which then bends to the right past the striking old E.L. Willis store building and winds over a bridge and into the far part of town, known as Little Hog Island. Six of the eight houses on Hog Island Lane were moved here as that barrier island depopulated in the face of erosion and storms during the early 1900s. 

Nassawadox Sawmill

The Nassawadox Sawmill

This is as good a place as any to pause and consider the natural and historical marvels just offshore. Barrier islands are sandy affairs that take shape along coastlines and protect the mainland from storm damage. Birds and other critters love the rich mix of salt marsh, tidal mudflats, and maritime forests out there. When it comes to “birds of conservation concern”—the ones experts keep an eye on because they’re at some level of risk—the barrier islands here have the highest diversity of species and density of population in all of Virginia. 

In fact, Virginia’s barrier islands are the longest stretch of undeveloped oceanfront land on the whole East Coast. They are mostly owned nowadays by the Nature Conservancy. Visitors can get out there only by boat, of course. There are charter captains hereabouts you can hire, but be sure to check the rules first—in some seasons, visitors are restricted to the beaches on the outskirts of islands to protect nesting birds raising their young farther inland.

These islands weren’t always undeveloped. For centuries, people lived out on Hog, Cobb, and other islands. Most of those folks put food on their tables by fishing, hunting, and gardening, while others worked at coast guard stations, lighthouses, and hunting lodges. Those lodges drew their share of rich and famous visitors. When President Grover Cleveland visited Hog Island, Willis Wharf was his departure point. In True Tales of the Eastern Shore, the historian Kirk Mariner relates a charming bit of oral history that sprang up around one of Cleveland’s visits:

Mary Anna Doughty came out of her house to call her four young sons to dinner only to find them shooting marbles in the lane with the President. When she called them in, Cleveland is said to have asked if he too could come, and happily joined the family for a meal of fried pies and milk.

Those days came to a close in the early years of the 20th century, thanks to a run of wicked storms that wreaked such havoc on the islands that the site of the original Hog Island Light, which once stood on terra firma, is now nearly a mile out to sea. Pretty much everyone had moved to the mainland by the 1930s. 

Eastern Shore Road Trips 2Heading back out Willis Wharf Road, you could choose to go past Seaside Road and into Exmore if you are in need of conveniences. The town, which sprang up in the wake of the railroad line’s arrival, has some shops, restaurants, and gas stations, both on the highway and in an old downtown. A classic dining experience there is the Exmore Diner, 4264 Main St.

When you get back to southbound Seaside Road, it will be a lengthy but lovely run down to Nassawadox, a community where local history buffs in the nonprofit Peninsula Tractor Organization have been working hard in recent years to turn the old Nassawadox Sawmill, 10150 Mill St., into a museum that tells the story of the important role forest products played in this area. As of this writing the museum is open mainly by appointment, as well as during once-in-a-blue moon special events.

If you’re in the mood to stretch your legs, find your way to the Brownsville Preserve (pictured up top), a 1,250-acre Nature Conservancy property east of town at 11332 Brownsville Rd. The William B. Cummings Birding and Wildlife Trail there runs through woodlands and marsh on a three-mile round trip. 

Back on Seaside Road, another lengthy run leads to the last fishing village on our checklist, Oyster. On the way there you will come to Machipongo Drive, which runs west into the town of that name. If you want to learn more about the history and culture of the barrier islands, find your way to the first-rate Barrier Islands Center on the far side of the highway, at 7295 Young St.

Another possible detour en route to Oyster is eastbound Indiantown Road, which leads out to Indiantown Park. This 52-acre stretch of green space and woodlands stands on a piece of the only Indian reservation ever established on Virginia’s Eastern Shore. The Gingaskin tribe (also known as the Accomacs) lived hereabouts between 1640 and 1813. 

The route into Oyster is six or so miles below Indiantown Road, at Sunnyside Road. Home to fewer than 100 residents, the town dates its history to a plantation established in 1737. The back part of the Methodist church, Travis Chapel, was moved from Hog Island. Be sure to wind your way up and around Crumb Hill Road to the Oyster Boat Ramp, where you can get out of the car, check out a couple of historic markers, and enjoy the views—that’s the tip of Mockhorn Island out toward the ocean. In the main part of town on the other side of the water you will find the short-but-sweet Oyster Village Horse Island Trail at the end of Sunnyside Road.

Return to southbound Seaside Road one more time to get down to the bottom of the peninsula. That road ends, after taking a big right turn, at the Eastern Shore of Virginia National Wildlife Refuge, located on the former site of an air force facility, Fort John Custis. You can choose here from among several hiking trails and an auto loop to wander through the 1,100 acres—the place is especially popular with birdwatchers. 


If you want to do some planning around this itinerary, here are some things to plug into your search engine:

• Eastern Shore of Virginia Tourism
• Accomack County
• Town of Wachapreague
• Northampton County Chamber of Commerce
• Peninsula Tractor (Nassawadox Sawmill Museum)
• Brownsville Preserve
• Barrier Islands Center
• Eastern Shore of Virginia National Wildlife Refuge 

This excerpt from Eastern Shore Road Trips #2: 26 MORE One-Day Adventures on Delmarva was posted by Claudia Colaprete on August 8, 2023 for Whimbrel Creations LLC/Secrets of the Eastern Shore. All rights reserved.

Thank you so much for spending a little time with this story and on this site!

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