Northern Eastern Shore & Upper Chesapeake Region
The Northern Eastern Shore & Upper Chesapeake Region of Maryland offers breathtaking landscapes, miles of scenic shoreline, vibrant and charming small towns, and award-winning Chesapeake Bay cuisine. Visitors can experience abundant outdoor recreation, wildlife, and nature. History buffs can make memories at unique heritage destinations that can touch your soul and take you back in time. And road trip fans can discover adventures along State and National Scenic Byways.
Select a Northern Eastern Shore & Upper Chesapeake County to Explore
Caroline County
Located on Maryland’s Eastern Shore of the Chesapeake Bay, visitors can relax and unwind in Caroline County. Among the scenic waterways and pristine countryside, discover a region brimming with rich history, outdoor excursions, and agri-tourism adventures. Caroline County offers outdoor recreation at Martinak and Tuckahoe State Parks and is part of the inspirational Harriet Tubman Underground Railroad Byway. Travel a byway, visit a farm, and enjoy small towns. You’ll soon be relaxed and refreshed and realize you belong here.
Outdoor recreation.
Picturesque landscapes will bring you here, but acres of unspoiled nature and waterways will keep you coming back. Caroline County offers hours of outdoor fun from paddling and peddling to sport shooting and fishing. Bring your bikes and pick up our Cycling Guide and explore our backroads. The county’s 8,000-plus acres of wildlife sanctuaries, nature preserves, parks and campgrounds and public and private campgrounds provide miles of hiking trails and plenty of places to camp, hunt, sport shoot and even ride horses.
Harriet Tubman Underground Railroad Byway.
Freedom seekers found shelter and assistance in Caroline County as they traveled along the Underground Railroad to Delaware. Explore by foot and by car the history and the lore of Harriet Tubman, Frederick Douglass and others. Sites include: Poplar Neck near Preston where Harriet Tubman made her greatest rescues; the Jacob Leverton Dwelling, (privately owned), the only documented Underground Railroad station building remaining on the Eastern Shore of Maryland; the Courthouse Square in Denton, the site of numerous incidents and the jail that held captured freedom seekers and Underground Railroad agents; and Hillsboro, the location of the permanent separation of Frederick Douglass family among various slaveholders.
Adkins Arboretum.
The gardens at Tuckahoe State Park are focused on sharing the appreciation and conservation of 600 plant species. It’s the only public garden that is native to the Mid Atlantic coastal plains.
Caroline County … you belong here.
Cecil County
Cecil County is located on the Upper Chesapeake Bay, midway between Philadelphia and Baltimore. Discover charming small towns, parks with miles of trails, specialty and antique shops, award winning restaurants, and inns. You can hike, bike, camp, bird watch, ride horseback, or drop a fishing line. Catch the action at the casino or at a family fun event. Five rivers, Chesapeake Bay and the C&D Canal can be explored by boat or by land. Experience panoramic views from Turkey Point Lighthouse on a bluff overlooking the Bay, or from the banks of the C&D Canal where ships from around the globe cruise.
Just a daydream away.
From one of the busiest canals in the nation, to the shorelines of five rivers, Cecil County has scenery and fun for the whole family. Discover a beautiful state park for hiking, biking, horseback riding and more! Enjoy our historic small towns brimming with charm. Experience farm destinations, sports action, and award winning food and wine!
Shop til you drop.
From antique specialty shops, and boutiques, to delicious food shops for candy, baked goods, homemade ice cream, and fresh grown fruits and vegetables, it's easy to shop the day away! Tucked along the streets of historic Chesapeake City, in the neighborly destination of Town of North East, and from one corner of the county to the next.
Historic Chesapeake City.
This 19th Century village with restaurants, shops, and boat tours is located along the banks of the C&D Canal. Wineries and Mt Harmon Plantation are nearby.
Town of North East.
This small town with vibe has restaurants, specialty shops, and foodie stops for chocolates, baked goods and local wine. Rent a kayak or enjoy the waterfront park with boat docks, picnic areas, and license-free fishing. Turkey Point Lighthouse is located nearby.
Dorchester County
Dorchester County … water moves us.
Adventure awaits.
With 1,700 miles of shoreline — more than any other county in Maryland — Dorchester offers everything from the mighty Chesapeake Bay to countless meandering waterways. Dramatic vistas of unspoiled countryside and marshland create the perfect backdrop for incredible sunsets. No wonder Dorchester draws outdoor enthusiasts, birders, photographers, hunters and anglers, cyclists, boaters, paddlers, and others from near and far. USA Today calls Blackwater National Wildlife Refuge one of the 10 best spots for “amazing wildlife watching,” while Outdoor Photographer magazine names the refuge one of the top 25 spots worldwide for nature photographers. Experience the boundless natural beauty for yourself by kayak or canoe, sailboat or powerboat, bicycle, or on foot.
See food our way.
Dorchester County is known for its delectable seafood – jumbo lump crab, rockfish, oysters, and more–fresh from our local waters. Many of our restaurants are waterside, and some are accessible by boat. You’ll also discover some surprises here, such as sophisticated restaurants tucked away down country lanes and in small towns. Whether you’re dining dockside, riverside, downtown, or in the country, you’ll enjoy that classic Eastern Shore hospitality. We’re also home to a lovely family-owned winery and vineyard. Don’t miss two of our biggest seafood events: the Taste of Cambridge Crab Cook-Off in July and the Seafood Feast-I-Val in August!
Blackwater National Wildlife Refuge.
Located 12 miles south of Cambridge, the refuge has more than 30,000 acres of woodland, rich tidal marsh, freshwater ponds and managed cropland — great for birdwatching, cycling, hiking, paddling, and nature photography. Blackwater National Wildlife Refuge is one of the chief wintering areas for migrating ducks and Canada geese using the Atlantic Flyway. Throughout the year there is a diverse population of birds, mammals, reptiles, and amphibians to enjoy watching and photographing, including bald eagles and Delmarva fox squirrels. The refuge features a full-service Visitor Center with a bookstore, restrooms, butterfly garden, and observatory, and a 4-mile Wildlife Drive with walking trails and a photo blind.
Harriet Tubman Underground Railroad Visitor Center.
The most famous “conductor” on the Underground Railroad, Harriet Tubman was born and lived in Dorchester County, Maryland, for her first 27 years or so. After she escaped slavery, she returned to the area, risking her life again and again, to lead dozens of friends and family out of slavery to freedom. Experience her story at more than 30 sites along the scenic, self-guided driving tour known as the Harriet Tubman Underground Railroad Byway, which winds for 125 miles through Dorchester and Caroline Counties on Maryland’s Eastern Shore before continuing into Delaware and on to Philadelphia. The Byway includes the Harriet Tubman Underground Railroad Visitor Center, which opened its doors to the public in 2017. In its first year, it drew nearly 100,000 visitors from every U.S. state and more than 70 countries, exceeding all expectations. This 17-acre park and visitor center is operated jointly by the Maryland Park Service and the National Park Service. The visitor center includes 10,000 square feet of exhibit space that shares Tubman’s story in compelling and interactive ways. There is also a nature trail and a large outdoor pavilion.
Kent County
Start an adventure in Kent County with exquisite waterfront dining and historic towns. Enjoy fishing, crabbing, sailing and kayaking on the Chesapeake Bay and scenic rivers. Experience local seafood, wine & spirits, unique shops, performing arts, galleries, farmers’ markets, and outdoor recreation.
Cuisine as fresh as it gets.
The benefits of eating locally sourced food are well lauded, from increased flavor and freshness to reduced waste, transit pollution and fuel consumption. Islanders naturally realize these advantages as their geographical limitations demand resourcefulness of everything the environment offers. While Kent County, Maryland, isn’t technically an island, it is nearly surrounded by water. Native tribes and early settlers thrived on its bounties from the sea and its fruitful soil. Fortunately, their traditions of self-reliance continue to prosper with residents today.
Picture-perfect moments along the waterfront.
When you visit the picturesque sites in Kent County, Maryland, you’ll want to keep your camera ready for unique selfies, breath-taking sunsets and large-format landscapes. Let’s face it, water is nature’s mirror for the sun and when the two meet, it’s a match made in photographic heaven. With Kent County’s 209 miles of shoreline, there are many locations where you can reflect. Crouch along the banks of rivers and creeks to frame their rippled surface with reeds; stroll waterfront promenades, wharves and piers to catch a couple walking hand-in-hand or a youngster casting a line in hopes of getting a big catch, and wander the docks of numerous marinas throughout the county for stylish nautical shots.
Eastern Neck National Wildlife Refuge.
With miles of nature trails, this refuge is popular for fishing, hunting, biking, and hiking. Spot wildlife along the way including fox, deer, waterfowl, raccoon, beavers, and 240 species of birds including the majestic Bald Eagle.
Rock Hall.
Road trip fans arrive in Rock Hall via the Chesapeake Country National Scenic byway. Boaters can dock, dine and discover this charming waterfront village. Stroll through the historic town, shop, book a charter, or rent a boat.
Queen Anne’s County
Queen Anne’s County … see what you’re missing.
Your adventure starts here.
Queen Anne’s County is home to captivating sunsets that illuminate the rural landscapes, thriving maritime communities, fresh local seafood, endless waterfront happenings and a variety of fun Chesapeake Bay adventures. Explore miles of diverse landscape along Cross Island, South Island, and Wye Island NRMA trail networks. Visitors can embark on a fishing charter voyage, or soak up dramatic waterfront sunsets along Kent Narrows, home to amazing local seafood eateries, live music, and tiki bars. Come join us and experience the peacefulness of over 200 miles of panoramic waterways graced with acres upon acres of pastoral landscapes.
Chesapeake Bay Environmental Center.
The environmental center offers diverse bird habitat along marshland, forests, ponds and shoreline. Visitors can experience a lecture, hike or bike a trail, and rent a kayak.
Cross / South Island Trail.
This extensive trail system has varied terrain through farmland, meadows, wetlands, and along the waterfront, with abundant wildlife and world class views.
Talbot County
Memories are made in historic Talbot County. Its waterfront beauty has an abundance of coastline for kayaking, fishing, crabbing, and sightseeing; hundreds of restaurants, bars and coffee shops for indulging; art and antiques to satisfy every interest; and tree lined, quaint towns in which to relax. Tour a museum, hike through Pickering Creek Audubon Center, take a ferry ride, bike along extensive routes and trails, or tour Easton’s Academy Art Museum.
On Maryland’s Chesapeake Bay.
Talbot County offers the perfect balance of rural simplicity and urban refinement. Home to sophisticated small towns, waterman’s villages and more than 600 miles of Chesapeake Bay waterfront, it’s the treasure of Maryland's Eastern Shore. There's a season for art, film, food and music festivals and a season for quiet and calm, ranking this as a go-to destination for both action-packed adventures and relaxing retreats.
Discover the history.
Talbot County is one of the oldest European settlements in the New World. When it was settled in the 1630s, new residents established tobacco plantations. Soon after, the county's 600 miles of shoreline made it an epicenter of the maritime industry—a culture preserved in such a way that it remains a special place to live and a unique vacation destination. A key site in the American Revolution, War of 1812, Civil War and Underground Railroad, Talbot County is still making history. American hero Frederick Douglass is among Talbot County's most notable native sons.
Explore the county.
For generations, visitors have come to Talbot County to experience the hospitality of its beloved towns and magnificent Chesapeake Bay views. The county offers the perfect combination of old and new — historic sites and new restaurants, nature-bound adventures and high end shopping, charming inns and stately accommodations. There is truly something here for everyone wanting to relax, reflect, and renew. Whether on a romantic retreat, a girls weekend getaway, a family vacation, or a team building business trip, Talbot County welcomes you with open arms.
Get back to nature.
As a singularly scenic community on the Chesapeake Bay, Talbot County offers every opportunity to get out on the water. Charter a sail or power boat, rent a hobie cat, take a fishing trip, enjoy a sunset cruise, paddle along in a canoe, a kayak, or a standup paddle board. But the water is just the beginning. Nestled in the shores of the county, are acres of preserved forests, wetlands, and wildlife, prime for hiking, exploring, bird watches, and nature walks. The county offers countless miles of bike trails — scenic and through the towns.
Chesapeake Bay Maritime Museum.
This 18-acre waterfront campus in St Michaels with the largest fleet of historic craft in existence shares stories of the Chesapeake Bay and generations of its people.
Avalon Theatre.
This historic 380 seat theatre, intimate listening room, and tent-like pavilion brings the best in performing arts to the Eastern Shore.