Rolling Through Chesapeake Country
One of America’s most beautiful stretches of road weaves through the heart of Talbot County. The Chesapeake Country All-American Road, a 400-mile scenic byway that ambles through the Eastern Shore, showcases Talbot County’s miles of tidal shoreline, verdant fields and forests, and vibrant small towns. The spine of the byway follows U.S. Route 50 through much of the county, but sidetracks will take you right to the water’s edge for spectacular Chesapeake views.
Bring your bike, too, since cycling is one of the most peaceful ways to explore this uniquely beautiful area. Pick up a copy of the Talbot County Bike Trails Map —or download it at TourTalbot.org — for routes that lead you to points of interest, from historic sites to waterfront vistas.
What are you waiting for? It’s time to hit the road!
Start at WYE MILLS
Start your journey in WYE MILLS, a small village anchored by the Old Wye Mill, a water-powered grist mill that still grinds flour the way it did in the late 17th century. Kids will love the hands-on activities, while adults will want to bring home a few bags of wheat flour, cornmeal, or buckwheat.
Drive through the quaint town to admire historic homes, large shade trees, and the Old Wye Church, a 1717 clapboard beauty topped with a bell tower. You’ll also find the diminutive Wye Oak State Park, a delightful spot to explore and picnic.
At the time it was felled during a thunderstorm on June 6, 2002, the namesake Wye Oak was the country’s largest white oak and was believed to be more than 400 years old. A cloned sapling was planted in its trunk on June 6, 2006.
On to EASTON
Continue a few miles to EASTON, the sophisticated center of Talbot County. You’ll be captivated by the diversity of historic homes lining the entrance into town, ranging from stately Federal-era mansions to colorful Victorians to charming Sears cottages.
Downtown Easton is in the midst of a renaissance. Check out the Prager Building, a former 19th century hotel that is home to some of Easton’s finest restaurants, a wine shop, and a cheerful juice bar. Directly across the street you’ll find the Talbot County Courthouse, which looks very much as it did when it was built in 1794.
Pause to explore the leafy grounds where you’ll find a spectacular bronze statue of Frederick Douglass, a Talbot County native who was born enslaved and returned a free man to share a message of hope and human rights.
Throughout town you’ll discover boutiques, restaurants, galleries, and a distinctive artsy vibe. At the Academy Art Museum, a small gem that focuses on American and European masters, visitors have a chance to do something rare — get up close to extraordinary works by artists like
Rembrandt, in a private setting without crowds.
As for live music, there are few better venues than the Avalon Theatre, which is celebrating its 100th anniversary in 2022 and ringing in our own era’s Roaring 20s. You can catch top-tier acts inside the restored art deco theater and check out emerging artists in the Stoltz Listening Room, an atmospheric lounge, and in a soaring outdoor pavilion.
Easton makes a perfect base for exploring Talbot County. Accommodations include charming historic inns, family-friendly hotels with pools, and a stately hotel at the center of town that’s been welcoming
guests since the 1940s.
Travel Next to ST. MICHAELS
You’re likely to spot wild turkey and white-tailed deer dashing from forest to fields as you travel U.S. Route 33 to reach ST. MICHAELS, just 10 miles away. You will also catch a dazzling glimpse of the Miles River, a tributary of the Chesapeake Bay, as you cross over the Oak Creek Bridge at Newcomb.
St. Michaels earned American glory when it thwarted an attack by the British Army during the War of 1812. Today you’re more likely to find yachts and powerboats than battleships, but the harbor itself remains virtually unchanged. This lively waterfront town has colorful historic buildings and dozens of locally owned shops and galleries.
The town’s many food options range from classic crab decks to fine dining restaurants and everything in between. This is an ideal place to set off on the water by booking a boat ride or renting a kayak or paddleboard. You can also walk or cycle the paved St. Michaels Nature Trail, a rail-trail that features
such charming highlights as a covered bridge.
At the Chesapeake Bay Maritime Museum, an 18-acre waterfront campus details the cultural and environmental history of the Chesapeake Bay region. Here you can visit a working boatyard and climb to the top of a retired and relocated lighthouse to see what life was like for the brave keepers who once lived here.
St. Michaels has dozens of choices for visitors who want to stay overnight, including short-term rentals, historic inns, marina-front rooms, and a world-renowned resort complete with golf, tennis, and a spa.
On to TILGHMAN ISLAND
Drive on about 13 miles to TILGHMAN ISLAND, an authentic waterman’s village that’s truly a world apart. Separated from the mainland by a drawbridge, the island is less than 3 square miles and is flanked by the Chesapeake Bay and the Choptank River.
Many residents still crab, fish, and oyster for a living the way generations have before them. The Tilghman Watermen’s Museum celebrates the contributions of the working watermen and offers insight into the island’s maritime identity.
The best way to soak up the serenity of this unique place is to stay in a waterfront room at one of the island’s relaxing inns. You can also plan a fishing excursion and dine on the freshest seafood in both upscale eateries and casual crab shacks.
Heading back out of town you will pass historic farmhouses and stands of old growth trees, where you
may spot a fleet-footed fox darting across a field. Instead of heading back to Easton, turn onto Route 329, still part of the scenic byway. It’s a shaded country lane that winds its way to a crossroads called ROYAL OAK. You’ll want to check out an antique shop that’s bursting with affordable treasures from clocks to garden urns.
Next Stop: OXFORD
Continue 3 miles along a quiet country road where bald eagles perch high in loblolly pines until you reach the Oxford Bellevue Ferry, the oldest privately owned ferry in the United States. This is the most atmospheric way to get to your next destination, the town of OXFORD. Cars are permitted on the small ferry, which crosses the Tred Avon River, a beautiful stretch of water where you have a good chance of seeing osprey swooping for fish.
Within minutes you will land in the heart of Oxford. This picturesque place with brick sidewalks, white picket fences, and exquisitely preserved historic homes also has a lively town dock and working marina. In the tiny downtown, the Oxford Museum chronicles life in the 18th and 19th centuries. There’s also a popular general store and a beloved bookshop specializing in mysteries.
As for restaurants, this town is a foodie magnet, known for waterfront eateries and chef-driven culinary experiences that attract a celebrity clientele, from politicians to hip hop artists. You can stay overnight in waterfront cabins, private short-term rentals, and historic inns, one of which George Washington patronized with a fellow signer of the Constitution.
Wrap It Up in TRAPPE
Conclude your road trip by taking Route 333, a peaceful two-lane road that weaves through gentle countryside, until you reach Easton and connect with Route 50. Follow this highway an easy 8 miles to TRAPPE, nestled at the southernmost tip of Talbot County.
Trappe is a small town with a big heart. Excellent restaurants (one housed in a historic bank) anchor the
historic main street, where you can see the childhood home of Baseball Hall of Famer Frank “Home Run” Baker.
This is a fine place to do some outdoor exploration. Country roads that spoke from town are prime cycling turf and the Bill Burton Fishing Pier south of town on the Choptank River is where you can join local anglers in pursuit of the Chesapeake Bay region’s famous catch.