Quintessential Chesapeake Bay Towns

World-class museums, thriving arts and cultural districts, history, nightlife, music and more make Baltimore the urban jewel of the Chesapeake Bay. Nicknamed a “Nest of Pirates” by the British, the people of Fells Point prefer the term “Privateers.” Whatever the name, Fells Point has been a hangout for sailors and travelers since the 1700s, and even today, it retains that swashbuckling attitude (Don’t believe us? Visit during the annual Privateer Festival!) just as it retains its original cobblestone streets and quaint architecture.

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From the soaring statehouse dome topped with a lightning rod made by Benjamin Franklin, on down the old bricked streets and past mansions to the continuous boat parade in Ego Alley, visiting Annapolis is a capital idea. Be sure to cross the harbor to the Maritime Republic of Eastport and visit the Annapolis Maritime Museum in the McNasby Oyster Packing House.

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Experience the full beauty of the Susquehanna River as it flows into the top of the Chesapeake Bay from the picturesque waterfront promenade with its charming Concord Point Lighthouse. Other not-to-be-missed sites are the world-renowned Havre de Grace Decoy Museum and the downtown shopping district.

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With breathtaking views of the Patuxent River and sunsets, this working waterfront community is a perfect mix of traditional and contemporary, served at a laid-back pace. Charter boats abound for fishing trips and the Calvert Marine Museum is home to river otters, Drum Point Lighthouse, tour boats, a paleontology gallery and lab, and more.

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Nestled along the Miles River, this chic historic waterfront town is home to museums and boutiques, gourmet restaurants and crab houses. There are plenty of opportunities to get out on the water with private boat tour companies or small boat rentals at the Chesapeake Bay Maritime Museum.  This spirited town is also home to several wineries, breweries, and distilleries.

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Located on the broad Choptank River in the heart of the Eastern Shore, this classic-yet-contemporary town retains its rich maritime history while adding a fun, modern slant. Sail on the skipjack Nathan of Dorchester, walk in the footsteps of Harriet Tubman, and enjoy the hip culinary and art scene in downtown.

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Once you have crossed the Bay Bridge to the Eastern Shore, it’s time to exhale and unwind. The wide open spaces, delightful bay views and a slower pace of life are all the ingredients you’ll need for relaxation. In Rock Hall you can enjoy a sunset sail with Shardana Sailing Charters, dine on fresh caught seafood, see a show at the Mainstay, and discover Eastern Shore heritage at the Rock Hall Museum in this friendly harbor town. At the family-friendly beach and the nearby Eastern Neck National Wildlife Refuge, there’s options to connect with nature, from hiking and biking, to birding, fishing and paddling. Public docking and several marinas make it a favorite stop if arriving via the water, and there’s several options for luxurious accommodations or down-to-earth lodging in a welcoming environment.

Nestled on the wide Chester River, this colonial port, National Historic District and small college town is a delightful place to enjoy a leisurely stroll on brick sidewalks to see the Georgian architecture, while stopping at boutiques, shops, cafes and historic inns. Saunter over to the docks. The town is known for Downrigging Weekend, a festival where you can explore tall ships from around the region, indulge in oysters and listen to bluegrass music. Experience a performance at the Garfield Center for the Arts and other sites in the esteemed Arts & Entertainment District. Most of the year, you can catch a sailing excursion on the Schooner Sultana, kayak the Chester River and explore the Lawrence Wetland Preserve to discover the Chesapeake Bay environments that make this place so special.

Kent Narrows is a lively waterfront destination filled with dock bars, laid-back crab houses, top-rated seafood restaurants and marinas. Located on the inlet between Kent Island and the Eastern Shore, the narrows is a popular destination for pleasure boaters, and there’s gorgeous water views almost everywhere you look. Book a fishing charter with Tuna the Tide, or take a sunset cruise and top it off with a crab feast. There’s plenty of places to stay after a fun-filled day and spirited evening entertainment. While you’re here, check out the Chesapeake Heritage and Visitors Center, a great place to get oriented and begin a bike ride on the Cross Island Trail where the panoramas are spectacular.

• At the top of the Bay, the small town charm of North East can’t be beat. Stroll Main Street to find shops filled with artisan crafts, gifts and antiques. A long-standing anchor of the town is Woody’s Crab House, a casual place to try local seafood and enjoy a crab feast. Explore the Upper Bay Museum, which holds a large collection of hunting and fishing memorabilia. The upper bay is historically known for waterfowl hunting. Rent a kayak from Bay Venture Outfitters to get out on the water and spot ducks and geese. When you’re finished exploring the town, travel south to Elk Neck State Park. North East is located at the head of the Elk Neck peninsula, which ends at a point with 100-foot high bluffs and sweeping views over the upper Chesapeake Bay. A trail takes you to the Turkey Point Lighthouse, a picture-perfect spot and rewarding culmination for your short hike.

• With a generous measure of 19th-century charm and a balance of modern activity, you’ll have lots of fun in Chesapeake City. This National Historic District, located on the busy Chesapeake and Delaware Canal, an active waterway connecting the two bays, has the best of both worlds. Wander the town to discover quaint boutiques and shops, then explore the Chesapeake City Museum and the C & D Canal Museum. Take a cruise on the canal with Chesapeake Water Tours to view the town from a new perspective or stretch your legs on the Ben Cardin C & D Canal Trail. 
• In the evening the town comes alive with revelry. Boaters traveling through the canal, dock for the night to experience its culinary scene and nightlife, with plenty of dining options in town, and nearby wineries and breweries. A stay at a historic inn to experience old world romance is the perfect nightcap to your night on the town.

Known as the Charter Fishing Capital of Maryland, this beachfront town has been a resort destination since the 1890’s when it had rail service from Washington, D.C. and Baltimore. Today it’s a family-friendly spot for outdoor discovery and relaxation on the lower Chesapeake. Take the kiddos to the Chesapeake Beach Water Park, swim and search for fossils at Breezy Point Beach, and bike the Chesapeake Beach Railway Trail on the former railroad bed turned nature trail. Stop by the Chesapeake Beach Railway Museum for tours, events and programs. 

And when you’re in the Charter Fishing Capital, you just gotta fish! Book a thrilling trip with Chesapeake Bay Storyteller Katherine Charter Fishing for an unforgettable adventure. And with all of that activity, you’ll need to relax at the Rod ‘N Reel Resort, Spa and Marina - or camp underneath a canopy of trees and connect with nature at the Breezy Point Beach & Campground.

St. Mary’s City is in a class of its own. This unique destination is Maryland’s original capital, a colony established with the values of religious freedom. Now a historic area and college town, the village includes a reconstructed colonial settlement, living history venue and museum. At the picturesque dock on the St. Mary’s River, tour the replica Maryland Dove, which transported the first colonists across the ocean to what is now Maryland.

While you’re in the area, see Point Lookout State Park at the southernmost tip of the Chesapeake’s western shore. Water trails, a swimming beach, Civil War sites and a lighthouse make this terminus at the confluence of the Potomac River worth the trip. Schedule a charter tour with Fish the Bay Charters and live the watermen’s life, photograph lighthouses, or reel in the day’s catch. On graceful fingers of land extending into the Bay and its rivers, waterfront crab houses, marinas, inns and guest houses dot the landscape on the Chesapeake’s southern coast.

An arts and entertainment district on the water, this delightful town is a great getaway to shop, stroll and dine. Art galleries, a homemade chocolate shop and a winery make this an enticing destination for foodies. The First Friday of every month the town celebrates with a concert, drinks, dessert, special exhibits and extended gallery hours.

Get your culture on and visit Tudor Hall and the Old Jail Museum with War of 1812 and antebellum stories. Sprinkle some outdoor adventure into your heritage tour. Meander through Leonardtown Wharf Park on the waterfront brick promenade, rent a kayak from Patuxent Adventure Center, and paddle a water trail on the Breton Bay. Then rest for the night at The Inn at Leonardtown for another day of exploration.

If you’re looking for a place to truly unplug and relax, Crisfield is it. On the Southern tip of Maryland’s Eastern Shore, the expansive views of the Chesapeake create a peaceful scene with amazing sunset views. The main thoroughfare through town ends at the Crisfield City Dock, where watermen unload their daily harvest, and passengers board charter fishing boats and ferries headed to Smith Island - an island out of time. The town is known for its annual National Crab Derby held every Labor Day weekend, and The Governor J. Millard Tawes Crab and Clam Bake. Explore the area’s maritime history at the J. Millard Tawes Historical Museum and see an authentic waterfowl decoy carving shop at the Ward Brothers Workshop.

A favorite destination for nature enthusiasts is Janes Island State Park, with its sandy beach accessible by boat. The park has miles of water trails weaving through wetlands waiting for the avid explorer. Stay overnight in park cabins or the campground and fish the waterways and view waterfowl.

For a unique adventure, immerse yourself in Chesapeake heritage and foodways on a tour with Experience Smith Island or Matchcoat Sojourner, and cruise to the only inhabited island in Maryland. Try a piece of Smith Island Cake, Maryland’s signature dessert with 8 - 10 layers, the perfect ending to your trip.

Head to Easton for a sophisticated Chesapeake destination steeped in art, history, culture, and culinary excellence. This arts and entertainment district features well-known anchors like the Avalon Theatre, with a full calendar of concerts and theatrical performances, and the Academy Art Museum, a premier art center. Galleries and studios dot the streetscape, interspersed with boutiques, restaurants and cafes of many ethnic varieties. The Tred Avon River runs through town, and transient slips are available at the Easton Point Marina. Stay the night at one of the gracious inns and B & Bs in historic homes.

Bring your bike to ride bike trails on scenic roads that lead you to Chesapeake views. A popular loop connects Easton with Oxford and St. Michaels, including a breezy trip across the river on the Oxford-Bellevue Ferry. Plan your visit for the Waterfowl Festival held in mid November to see decoy carving in action, and experience exhibits, music and Chesapeake Bay cuisine.

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