I’ve chased adventure by kayak down the Mississippi and skied pristine slopes near and far, but nothing rivals the intimate freedom of a well-planned bike journey. There’s an intoxicating simplicity in compressing your world into compact panniers and surrendering to the rhythm of the road—no deadlines, no obligations, just the hypnotic spin of wheels against asphalt and the quiet anticipation of what lies beyond the next bend.
Though I call Staunton home, Virginia’s Chesapeake Bay region has held my imagination captive for years. I’m especially drawn to both the Northern Neck and the Rappahannock River that offer the cyclist’s dream trifecta: flat, forgiving terrain; breathtaking water views; and a string of characterful towns separated by perfect riding distances. Those in the know gravitate toward the majestic 98-mile loop connecting Tappahannock, Urbanna, and Kilmarnock—a circuit rich with wineries, waterfront dining, historic architecture, and immersive natural beauty.
My plan: stretch this journey across several days, savoring the region’s distinctive blend of history, cuisine, and coastal splendor rather than racing through it. Why rush paradise?
DAY ONE: Tappahannock Beginnings
The 150-mile drive from Staunton deposits me in Tappahannock by mid-morning. This riverfront town of 2,200 souls welcomes with an architectural gallery of imposing 18th- and 19th-century homes—Colonials, Federals, and Victorians standing proud along tree-lined streets. I wander among these grand sentinels before finding Java Jack’s Café, a Cape Cod bungalow dressed in tropical pastels that feels transported from Key West. I can’t resist the “Come In, We’re Awesome” sign.
Inside the diner-meets-beach-cottage interior, I order the “Rivah” Omelet—a decadent creation stuffed with Chesapeake Bay crabmeat, creamy provolone, spinach, and tomatoes. Two cups of espresso-fortified coffee later, I’m finally ready to mount my bike and begin this 40-mile day.
Java Jacks’ Rivah Omelet is stuffed with crabmeat, provolone, spinach, and tomatoes and comes with signature jacks, bacon, fruit, and hash browns. Grits and toast are add-ons.
Leaning into the coffee craze, Java Jack’s coffee flights offer a variety of flavorful brews.
A quick detour along Water Lane reveals St. Margaret’s School, its Georgian Colonial manor from the 1760s and main hall from 1840 overlooking the broad Rappahannock. I pause appreciatively for the view, then I’m off, first navigating through Hoskins Creek’s reedy tidal wetlands and a stretch of modern commerce along U.S. 17 South before the landscape dramatically transforms.
Essex Mill Road delivers me into cycling nirvana—narrow, European-like backroads threading through cool forest canopies, tidal marshes, and sprawling cornfields. The communities of Dragonville and Shanghai appear like time capsules from another century. Traffic here is so scarce that the only soundtrack is the rising chorus of birds, frogs, and insects emanating from enchanted bald cypress forests in Dragon, Briery, and Church Swamps.
Spring migration brings yellow-rumped warblers—locally nicknamed “butter butts” for their distinctive hind-quarter markings—trilling sweetly from hidden perches. I pedal onward, crossing U.S. 17 again before peddling into Urbanna along rural fishing outposts decorated with weathered boats, buoys, and rusty crab cages.
Downtown Urbanna unfolds along Old Virginia Street—a charming collection of repurposed warehouses and historic homes now housing boutiques and eateries. My destination, a Cape Cod Airbnb cottage called “Lil Bit,” sits just blocks from downtown on Queen Anne’s Cove. My wife Laura has arrived ahead of me, and together we celebrate on our private dock with glasses of award-winning 2019 Petit Verdot Reserve from nearby Ingleside Vineyards in Westmoreland County. Egrets and herons patrol the shallows as the setting sun paints coruscated clouds in soft pink and violet across the
mile-wide Rappahannock.
Dinner takes us to The Urban Oyster, set in a renovated brick building on Cross Street. At the farmhouse-style bar, we sample regional craft beers alongside house-baked pretzels, blue crab bisque, red snapper nuggets with sweet Thai sauce, and impossibly fresh local oysters.
Aerial shot of the Rappahannock River Valley National Wildlife Refuge. The area is particularly known for attracting migratory birds and waterfowl, as well as being a habitat for threatened and endangered species.
Sailboats at the marina in Urbanna at sunrise.
DAY TWO: Urbanna to Irvington
Big Oak Café provides a Bloody Mary brunch with chipped beef biscuits and gravy worthy of a Southern grandmother’s kitchen. Fortified, I embark on a leisurely exploration of Urbanna’s Historic District with its 65 notable buildings, including the awe-inspiring Lansdowne plantation that dates to 1750, now privately owned.
Crossing Urbanna Bridge reveals a Rockwellian panorama of traditional boat houses and marinas filled with sailboats and yachts and runabouts before the landscape transforms to vast tracts of lowland corn, peanut, and soybean fields beneath a radiant blue dome. I pass modest farmhouses and intermittent corridors of dense, marshy forest before reaching the intersection with State Route 33.
In Topping, I turn onto a dusty gravel drive leading to Merroir’s Tasting Room—the waterfront jewel of Rappahannock Oyster Co.’s original historic bivalve farm on Locklies Creek. With unobstructed views of the Rappahannock, I order a crisp pilsner and six briny Chincoteague Olde Salt oysters. Laura joins me, but cautions me against overindulging before my afternoon ride. Nevertheless, I browse the menu and can’t resist ordering pan-seared scallops with crispy hominy and avocado cream sauce. No surprise—they’re a 10 out of 10.
The next challenge looms: the narrow, two-mile-long Robert O. Norris Jr. Bridge that feels as if I’m at least a mile over the Rappahannock. Laura follows in our car, easing my anxiety as I maintain focus while stealing occasional glances at the river below, where boats cut through the water, and an osprey—maybe it’s a bald eagle?—circles beneath high, shredded-cotton clouds.
Oystermen harvest fresh oysters from the Rappahanock River, destined for a river-to-table experience.
A scenic view and tasty brew from the dock at Merroir.
Merroir, Virginia’s most unique tasting room.
Safely across in Lancaster County, I cruise through White Stone, where revitalized historic buildings house cafés, galleries, and boutiques. Despite the full meal at Merroir, Chesapeake Doughnuts’ chocolate Snickers—a cake doughnut topped with chocolate frosting, peanut pieces, and caramel drizzle—proves irresistible.
The final two miles to Irvington take me over Carter’s Creek, past upmarket vacation homes and enchanted riparian forests, before I swing left onto King Carter Drive. I arrive at the historic 1890s school-turned-Hope & Glory Inn, where Laura awaits on the porch of our luxury cottage, one of seven on the property. It’s sumptuous, with shabby chic décor and lush amenities. There’s even a fenced clawfoot tub tucked deep in the garden for moonlight baths. We toast my 20-mile ride with glasses of Kilmarnock’s Good Luck Cellars’ 2022 Vignoles—a fruit-forward dry white with citrus notes that earned a 2024 Virginia Governor’s Cup silver medal.
Evening finds us at White Stone’s understated Adrift restaurant, where owner-chef Devin Rose (an alum from The Inn at Little Washington) creates magic with local ingredients. I begin with Steamboat Wharf oysters topped with trout roe, pickled watermelon rind, and kimchi sorbet, followed by a showstopping entrée of Tom’s Cove clams over squid ink tortellini with house-cured Autumn Olive Farms Ibérico chorizo. It’s a dock-to-dish delight.
Chesapeake Doughnuts offers a mind-bending array of flavors—honey pistachio, carrot cake, Samoa, stuffed French toast, chocolate cherry cheesecake, Snickers, and more.
DAY THREE: The Final Stretch to Tappahannock
Morning begins at The Local, Irvington’s coffee café, with a single-origin brew and a gourmet bacon, egg, and cheese sandwich on a house-baked everything bagel. Then it’s time to tackle the final, challenging 50-mile leg back to Tappahannock.
The route begins along Irvington Road through farmland and rural neighborhoods to Kilmarnock, where I’m surprised by a vibrant, historic downtown filled with more than 50 establishments—art galleries, pubs, and more—housed in structures ranging from 1920s Cape Cod revivals and Craftsman bungalows to 18th-century Colonials and Victorian beauties. I scribble mental notes about where I intend to return—Front Porch Coffee House, the Kilmarnock Inn, Car Wash Café, and Good Luck Cellars make the list.
Northwest of town, I follow gently rolling backroads through maritime forests that open onto serene farms and bright-green pastures. Tiny villages with names like Brook Vale, Lively, Nuttsville appear and recede, their old homes and outbuildings in various stages of decay or renewal.
The landscape’s expansiveness and the cool, salt-tinged air lull me into a meditative state—a trance of rhythm, breath, scenery, and motion. Near Warsaw, the terrain shifts to wetlands and tidal waterways dotted with migratory waterfowl and wading birds.
Victory feels within reach as I coast onto Warsaw’s revitalizing Main Street to meet Laura at Relish Restaurant & Wine Bar. We indulge in Fat & Happy Oyster Co. offerings. They’re almost like an oyster flight—prepared raw, roasted, and fried—plus they’re served with Relish’s famous pimento cheese.
The final stretch takes me along Route 3 through the 9,030-acre Rappahannock River Valley National Wildlife Refuge—a sanctuary where I spot red-tailed hawks perched on snags, wading great blue herons, and soaring ospreys.
The mile-long Downing Bridge delivers me back to Tappahannock, offering a grand finale of sunset views over the mighty Rappahannock. Exhausted but triumphant, I arrive at the Essex Inn, an imposing Greek Revival manor built in 1851 and recently transformed into a boutique hotel by Greg and Jennifer Huff, native North Carolinians who’ve made Tappahanock their home. Laura and I settle into our well-appointed courtyard-facing suite that occupies meticulously upgraded 19th-century servants’ quarters.
Period antiques in the foyer at the Essex Inn.
The elegant living room at the Essex Inn.
For our celebration dinner, we cross the street to 1710 Tavern—purportedly Virginia’s oldest—where exposed beams, original fireplaces, and leaded glass windows transport us to Colonial times. It’s also been revitalized by the Huffs, who’ve preserved its rustic, old-world charm while infusing it with a modern vibe.
Over a four-course, wine-paired tasting menu highlighted by succulent pekin duck breast with foie gras, we toast the completion of my 110-mile journey. This perfect cyclist’s loop—connecting historic towns, Chesapeake Bay waterways, and fresh-caught seafood—captures the essence of Virginia’s Northern Neck and satisfies both wanderlust and appetite in equal measure.
1710 Tavern boasts impeccable service and a menu that focuses on fresh and seasonal dishes—and stellar desserts.
1710’s bar program includes its signature smoked old fashioned, where a torch ignites wood chips, imparting rich flavor.
1710 Tavern boasts a robust wine list, with many varieties from the Commonwealth.
From 1710 Tavern, bottom: grilled bone-in pork chop with herb butter, fried Brussels sprouts, and roasted vegetables. Top: rosemary-garnished lamb with butternut squash purée. A glass of red wine and a smoked old fashioned complement the meal.
All About the NNK
The Northern Neck refers to the northernmost of three peninsulas—traditionally called “necks” in Virginia parlance—on the western shores of the Chesapeake Bay. The area encompasses four counties: Lancaster, Northumberland, Richmond, and Westmoreland. It’s also affectionately referred to as NNK, its acronym. NNK swag—mugs, t-shirts, coasters, puzzles, and car magnets—is available on NNKShop.com. Sadly, the counties on the other side of the Rappahannock—Essex, Gloucester, Mathews, and Middlesex don’t have a branded moniker. Ideas? Send them to [email protected]
5 Things Your Can’t Miss
Fish Hawk Oyster Bar, Irvington: Grab a seat at this lively, watermen-themed poolside bar area at the historic Tides Inn. Expect local raw oysters, gourmet burgers, craft brews, creative cocktails, and stellar views of Carter’s Creek. TidesInn.com
Historic Christ Church & Museum, Weems: The Georgian-style brick church dates to 1735 and may be the state’s most pristine example of British Colonial ecclesiastical architecture. Tours encourage visitors to explore its original wood pews, pulpit, grounds, and more. ChristChurch1735.org
Ditchley Cider Works, Kilmarnock: Enjoy small-batch ciders at this historic site anchored by a brick, Georgian-style manor from 1688. Ciders are crafted entirely from heirloom, estate-grown apples. DitchleyCiderWorks.com
Kilmarnock Antique Gallery: A treasure trove of vintage items from more than 100 vendors awaits in the 22,000-square-foot downtown showroom. The 13-time Best of Virginia winner is famed for its world-class oyster plate collection. Virginia-Antiques.com
Urbanna Historical Walking Tour: The self-guided trek includes 14 historical sites and 18 placards that tell the story of the nearly 350-year-old town. Download the app for GPS directions and informational videos from town historian Larry S. Chowning. Urbanna.com
Gear Up For A Great Ride
Quality equipment can make or break a trip. This checklist of go-to gear will tee you up for success.
Trek Domane AL 2 Gen 4 Bike
This startlingly well-equipped ride lets you crush miles with an ease and comfort unheard of for the price point (around $1,200). The sleek aluminum frame looks great and is outfitted with components fine-tuned for comfort, control, and responsiveness.
TrekBikes.com
MAAP Pro Race Mitts
These stylish gloves will keep your hands fresh and protected on long warm-weather rides. Mesh backing and perforated elastic interface palms are light, comfortable, and breathable. $90. MAAP.cc/us
Rudy Project Eyewear
The Italian-based innovator has outfitted pro cyclists with shades for
40 years. Its ultralight “Turbolence” model combines wind-cutting coverage with photochromic lenses that self-adjust to filter sunlight. $255. RudyProjectNA.com
Rudy Project Venger Helmet
Fashionable headgear that feels so
light and comfortable it seems to vanish. A cutting-edge impact protection system provides cranial protection, while a layered frame maximizes airflow and sweat-wicking. $250. RudyProjectNA.com
Specialized S-Works Torch
Cycling Shoes
Supreme adjustability and a form-fitting upper with optimized ultralight materials for different areas of the foot boosts pedaling efficiency and comfort on long rides. Stiff carbon soles maximize power. $100–450. Specialized.com
Ortlieb Back Roller Panniers, Pair
Keep your goods dry and protected on your rear rack with a pair of durable and waterproof panniers. $200. REI.com
This article originally appeared in the June 2025 issue.
