The City of Chesapeake and the Chesapeake Bay estuary are packed with things to see and do.

Known for its beautiful natural scenery and rich cultural and historical significance, Chesapeake is home to over 20 miles of waterways, canals, lakes, and rivers, as well as several parks and outdoor recreation areas for hiking, mountain biking, horseback riding, and picnicking. There are also plenty of galleries, museums, and restaurants.

1. Academy Art Museum

Academy Art Museum
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Housed in a beautifully preserved early 19th-century schoolhouse, the Academy Art Museum in Easton, Maryland houses a permanent and rotating collection of local and national artists and hosts a series of concerts, dance, and lectures.

Founded in 1958 to enhance the appreciation of the arts and culture of the Eastern Shore, the museum features a permanent collection of artworks from both local and international artists and works paper by modern American and European masters.

The collection also holds significant photographs, prints, and drawings by prominent individuals such as Robert Rauschenberg, Pierre Bonnard, and Martin Puryear and offers a broad spectrum of exceptional cultural and educational offerings such as visual and performing arts classes for adults and children, lecture series, concerts and more.

106 South St, Easton, MD 21601, Phone: 410-822-2787

2. Adkins Arboretum

Adkins Arboretum
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Based in the Tuckahoe State Park in Ridgely, Maryland, the Adkins Arboretum is a beautiful 400-acre native garden and preserve with a living collection of more than 600 native plant species, and over five miles of meadow and woodland paths.

Established to promote the appreciation and conservation of native plants in the Chesapeake Bay region, the botanical garden offers a variety of educational programs, guided walks, demonstrations, lectures, art exhibitions, and seasonal community events.

The Arboretum also features a gift and book shop and sells a variety of native plants featured in the garden.

12610 Eveland Rd, Ridgely, Maryland 21660, Phone: 410-634-2847

3. American Cruise Lines

American Cruise Lines
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American Cruise Lines, Inc. is a small-ship cruise line that operates twelve small cruise ships along with the Eastern Seaboard and Western Seaboard and the Mississippi-Ohio and Columbia-Snake river systems of the United States. Offering a authentic All-American experience, the fleet is made up of the newest and most environmentally-friendly small cruise ships and riverboats in the country, and provides a plethora of world-class services such as award-winning cuisine and fine wines, beautiful accommodations with high-end amenities and facilities, daily entertainment ranging from lectures to live music, and highly personalized service and hospitality. Phone: 800-460-4518

4. American Chestnut Land Trust

American Chestnut Land Trust
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The American Chestnut Land Trust protects 3,000 acres of natural landscapes in Calvert County, Maryland, which include farmlands, wetlands, and dense hardwood forests, as well as 22 miles of hiking, mountain biking, and horseback riding trails in the Parker Creek Preserve. Located about an hour’s drive from Washington D.C., the pristine natural area also features several historic structures, interpretive trails, and community farm and guided canoe trips. The southern section of the preserve has four primary hiking trail loops daisy-chained together, which provide several excellent hikes of varying lengths that are suitable for all levels of hiker.

676 Double Oak Rd, Prince Frederick, Maryland 20678, Phone: 410-414-3400

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5. Annapolis Yacht Club

Annapolis Yacht Club
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Founded in 1886, the Annapolis Yacht Club is a year-round premier private yacht club that provides a wide range of quality services for club members. From its humble beginnings as a canoe club, the world-class yacht club offers a variety of services such as sailboat racing, a vigorous junior sailing program, cruising for sailors and powerboaters, fun and educational winter activities, first-class dining and banquet facilities, and social events throughout the year. Set on the banks of Spa Creek in Annapolis Harbor, the clubhouse has a beautifully appointed dining room where members can savor award-winning cuisine and fine wines from around the world against a backdrop of spectacular harbor views.

2 Compromise St, Annapolis, Maryland 21401, Phone: 410-263-9279

6. C&D Canal Museum

C&D Canal Museum
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The C&D Canal Museum explores the history of the 14-mile-long C&D Canal that was built in the 19th century to connect Delaware Bay and the Chesapeake Bay. The historic waterfront site is owned and operated by the U.S. Army Corps of Engineers and explores the history of the world’s third busiest shipping canal and features interactive displays, fascinating videos, exciting exhibits about the building of the canal. The museum is based in the original pump house, which is listed on the National Register of Historic Places and dates back to the 18th century and was used to control the water levels in the locks of the first canal.

815 Bethel Rd, Chesapeake City, MD 21915, Phone: 410-885-5622

7. Calvert Cliffs State Park

Calvert Cliffs State Park
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Calvert Cliffs State Park is a public reserve and recreation area in Lusby that protects and preserves the Calvert Cliffs, where more than 600 species of fossils from the Miocene era have been found. Extending for 24 miles along the eastern flank of the Calvert Peninsula, the cliffs form part of a rugged shoreline that was once submerged beneath a shallow sea and is now a treasure chest of prehistoric gems such as ancient sharks’ teeth and oyster shells. The massive cliffs after which the park is named were formed over 20 million years ago and today reveal the remains of prehistoric species, including enormous rays, seabirds, whales, and sharks. The day-use park has a lovely sandy beach, a recycled tire playground, freshwater, and tidal marshlands and over 13 miles of hiking trails and offers recreational activities such as fishing, swimming, and beachcombing.

10540 HG Trueman Rd, Lusby, MD 20657, Phone: 443-975-4360

8. Captain John Smith Chesapeake National Historic Trail

Captain John Smith Chesapeake National Historic Trail
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The Captain John Smith Chesapeake National Historic Trail is a series of water routes that trace the paths and places that Englishman John Smith and a small crew of adventurers explored over 400 years ago. The team set out between 1607 and 1609 and mapped and documented nearly 3,000 miles of the Bay and its rivers, visiting thriving Native American communities and gathering relevant information about new lands along the way. Extending around 3,000 miles along the Chesapeake Bay and its tributaries, the Captain John Smith Chesapeake National Historic Trail was designated as a national historic trail in 2006 – the first national water trail of its kind and one of only two National Historic Trails.

Yorktown, VA 23690, Phone: 757-898-3400

9. Chesapeake Bay Maritime Museum

Chesapeake Bay Maritime Museum
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The Chesapeake Bay Maritime Museum in the lovely Eastern Shore town of St. Michaels celebrates all things maritime and houses the most extensive collection of historic Chesapeake Bay watercraft from drake-tail oyster boats to log canoes and skipjacks. Based on a site that once housed seafood packing warehouses and workboats, the 18-acre waterfront museum has a working boatyard where historic wooden boats are lovingly restored to their former glory. Visitors can apprentice with a shipwright to learn the trade hands-on. The interactive museum also features a beautiful old lighthouse, a butterfly garden, a variety of exhibits highlighting the Bay’s history, and living shoreline.

213 N Talbot St, St Michaels, MD 21663, Phone: 410-745-2916

10. Chesapeake Wine Trail

Chesapeake Wine Trail
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The Chesapeake Bay Wine Trail is a wine-lovers trail that winds through Virginia’s Chesapeake Bay wine region and visits nine wineries for tastings and tours. Encompassing the Northern Neck and Middle Peninsula of Virginia, the trail passes well-known wineries such as Caret Cellars, General’s Ridge Vineyard, Good Luck Cellars, Ingleside Vineyards, Jacey Vineyards, The Dog and Oyster, and Vault Field Vineyards. Visitors can enjoy tours of the wineries and taste some of their top vintages along with local farm-to-table fare in beautiful settings.

Caret Cellars, 495 Meadow Landing Lane, Caret, VA 22436, Phone: 540-413-6454

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11. Chester River Packet Company

Chester River Packet Company
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The Chester River Packet Company offers charters cruises and private events on the scenic Chester River on Maryland’s Eastern Shore. Cruises are run on the 65-foot classic yacht, River Packet, a beautifully restored 1920-style tour boat with open-air forward and upper decks, a climate-controlled salon, and ample seating for private events and functions. The 108-passenger vessel is ideal for dinner cruises and private parties and works in conjunction with Occasions Catering, who supply catering and event hosting services. Public charter cruises are offered on Thursday and Friday evenings; Saturday afternoons and evenings; and for Sunday Brunch.

High Street Town Dock, Chestertown, MD 21620, Phone: 410-635-0321

12. Delmarva Balloon Rides

Delmarva Balloon Rides
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Take to the skies and soak up the beauty of the Chesapeake Bay from the air on a hot air balloon trip with Delmarva Balloon Rides. The family-owned and operated company has been offering memorable balloon adventures for over ten years and provides a variety of flight packages from pre-sunrise and night flights to private proposal flight, corporate advertising and banner flights, and special celebrations such as weddings, anniversaries and birthday. Additional services include photography, champagne toasts, and the company also offers balloon camps and educational programs where children can learn about the basics of ballooning.

1137 Little Creek Rd, Chester, MD 21619, Phone: 301-814-3297

13. Eastern Neck National Wildlife Refuge

Eastern Neck National Wildlife Refuge
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Eastern Neck National Wildlife Refuge is a 2,286-acre island located at the confluence of the Chester River and the Chesapeake Bay and is part of the Chesapeake Marshlands National Wildlife Refuge Complex. Established in 1962 as a sanctuary for migratory birds, the refuge still provides protection and a natural habitat for over 240 species of birds, including transitory peregrine falcons, bald eagles, and tundra swans. Along with bird watching, the refuge offers a range of outdoor recreational activities, such as hiking, mountain biking, boating, fishing, crabbing, and seasonal hunting.

1730 Eastern Neck Rd, Rock Hall, MD 21661, Phone: 410-639-7056

14. Harriet Tubman Underground Railroad State Park and Visitor Center

Harriet Tubman Underground Railroad State Park and Visitor Center
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The Harriet Tubman Underground Railroad State Park and Visitor Center honors American abolitionist and political activist Harriet Tubman and tells the story of her life and work. Located a short drive from Cambridge and surrounded by the landscapes where Tubman lived and worked, the park features a 10,000-square-foot Visitor Center, which houses an array of engaging and enlightening multimedia exhibits about her life. The center is a starting point for the scenic, self-guided driving tour of the Harriet Tubman Underground Railroad Byway, which features 36 sites related to Tubman and the Underground Railroad on Maryland’s Eastern Shore. The park also features meditation garden, nature trails, and an outdoor pavilion.

2 Rose Hill Place, Cambridge, MD 21613, Phone: 410-228-1000

15. Havre de Grace Decoy Museum

Havre de Grace Decoy Museum
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Set banks of the Susquehanna Flats, the Havre de Grace Decoy Museum celebrates the decoy - a central element of Chesapeake culture for centuries - and preserves the historical and cultural legacy of water-fowling and decoy-making on the Chesapeake Bay. The museum houses a world-class collection of working and decorative Chesapeake Bay decoys, along with a variety of folk and exceptional art models and offers guided tours and demonstrations on decoy-making. The museum has over 1,200 decoys and decorative carvings on display with works by masters such as Bob McGaw, R. Madison Mitchell, and the Ward Brothers.

215 Giles St, Havre De Grace, MD 21078, Phone: 410-939-3739

16. Historic St. Mary’s City

Historic St. Mary’s City
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Historic St. Mary’s City is a living history area, museum complex, and pristinely preserved English colonial archaeological site that showcases what was once a former frontier town and Maryland’s first colonial settlement and capital city. Surrounded by 800 acres of beautiful landscapes, the museum complex has been reconstructed to look like the original colonial settlement and explores the cultural and historical importance of the fourth permanent English settlement in North America. The complex is internationally recognized archaeological research area which has seen over 200 digs in the past three decades, and special events held throughout the year offer one-of-a-kind opportunities for visitors to explore the lifeways and culture of the region’s Native American peoples.

18751 Hogaboom Lane, St. Mary’s City, MD 20686, Phone: 240-895-4990

17. Sandy Point State Park

Sandy Point State Park
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Resting along the Northwestern shore of the Chesapeake Bay Bridge in Anne Arundel County, Sandy Point State Park is a public recreation area that is home to the historic Sandy Point Farmhouse and the Sandy Point Shoal Light. The 786-acre Maryland State Park has several beautiful beaches and picnic areas that are popular spots for swimming, fishing, crabbing, wildlife viewing, picnicking, and soaking up the breathtaking scenic water views of Chesapeake Bay. The park also has a marina store and boat rentals, and over four miles of hiking trails for all ages and skill levels.

1100 E College Pkwy, Annapolis, MD 21409, Phone: 410-974-2149

18. Smith Island

Smith Island
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Smith Island is an island about 12 miles off the shore of Crisfield in the Chesapeake Bay that was discovered by Captain John Smith and settled about 350 years ago. The cultural treasure is only accessible by boat and can be reached by ferry from Crisfield and Point Lookout State Park, and there are a few slips at Smith Island Marina for personal watercraft. Named after Henry Smith of Jamestown, the island has around 200 residents living permanently, many of whom harvest fresh seafood, mostly in the form of crabs, clams, and oysters. The island is also home to over 4,000 acres of marshland, which are managed as the Martin National Wildlife Refuge.

Crisfield, MD

19. St. Clement’s Island-Potomac River Museum

St. Clement’s Island-Potomac River Museum
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The St. Clement’s Island–Potomac River Museum tells the story of how Maryland was found by the first brave English colonists who sailed across the Atlantic Ocean in two small wooden boats. The nationally-accredited museum features an array of informative exhibits about the 370+ years of island history, including a 13-minute orientation film, and special events and programs throughout the year. The museum also explores the history of the Blackstone Lighthouse and features an authentic one-room schoolhouse dating back to circa 1820, a Potomac River Dory Boat Exhibit, and picnic tables on the waterfront with beautiful views.

38370 Point Breeze Rd, Coltons Point, MD 20626, Phone: 301-769-2222

20. Tangier Island Cruise

Tangier Island Cruise
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Explore the small, picturesque island of Tangier on a cruise aboard the Steven Thomas, a 90-foot, 300-passenger boat with an air-conditioned lounge, an upper sun deck, a snack bar, and modern restrooms. The historic and charming island was settled by John Crockett in 1686 and is home to a quaint town with narrows streets and about 600 residents who still live off the bounty of the surrounding sea as fishermen and speak a unique English Restoration era dialect of American English. The island also boasts some of the most beautiful scenery on the Chesapeake Bay and Tangier Sound, including the three small islands of Fox Island, Watts Island, and Port Isobel.

1001 W Main St, Crisfield, MD 21817, Phone: 410-968-2338

21. Thomas Point Shoal Lighthouse

Thomas Point Shoal Lighthouse
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The Thomas Point Shoal Lighthouse, also known as Thomas Point Shoal Light Station, is a historic lighthouse in the Chesapeake Bay and the only active screw-pile lighthouse left in the Bay. Built in 1875, the hexagonal structure guards the entrance to South River and resembles a quaint cottage standing in the middle of the Bay. The National Historic Landmark can be visited by docent-led tours on a 30-minute boat ride to and from the lighthouse and is one of the most photographed lighthouses in America. The Thomas Point Shoal Lighthouse continues to be an active and Coast Guard-maintained aid to navigation for the Chesapeake Bay.

Thomas Point Shoal, Annapolis, MD 21403, Phone: 415-362-7255

22. Tilghman Island

Tilghman Island
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Nestled between the Chesapeake Bay and the Choptank River, Tilghman Island is a traditional waterman and quintessential historic American waterfront village on the Eastern Shore of the bay. Established in 1650 and accessed via a drawbridge, Tilghman Island is an authentic waterman's village where residents lived off the bounty of the ocean as crabbers and fishermen and still do so today. Boasting pristine natural landscapes, the island is home to the Tilghman Island Waterman's Museum and the Phillips Wharf Environmental Center, which explore and detail the area's maritime heritage. Tilghman Island also offers deluxe accommodations, award-winning seafood-centric dining, world-class fishing and sailing, and gracious hospitality.

Talbot County, Maryland

23. Virginia Barrier Island Center

Virginia Barrier Island Center
© Virginia Barrier Island Center

The Virginia Barrier Islands are a string of long, narrow, low-lying barriers islands made up mostly of sand and scrub that is situated along the entire eastern coast of Virginia and are separated from the mainland by shallow marshy tidal bays. Stretching from Assateague Island to Fisherman's Island, these 23 uninhabited shifting islands of sand, marshland and lagoons form an essential ecological region that makes up the Virginia Coast Reserve. The Barrier Islands Center (BIC) was opened in 2002 and is dedicated to highlighting Virginia's unique coastal history through a variety of exhibits and more than 7,500 artfully displayed artifacts.

7295 Young St, Machipongo, VA 23405, Phone: 757-678-5550

24. Virginia Oyster Trail

Virginia Oyster Trail
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The Virginia Oyster Trail celebrates tasty mollusk that Virginia is famous for. Established by the Hope & Glory Inn and Vineyard’s owner, Dudley Patteson, the Virginia Oyster Trail is an adventure that encompasses several attractions around the Chesapeake Bay and the state, ranging from boat tours and historical sites to visiting restaurants, oyster stands, and vendors for oyster tasting. Activities on the trail include tasting gourmet fare and freshly shucked oysters at the Hope and Glory Inn’s award-winning restaurant, oyster and wine pairing at the Dog and Oyster Vineyard, browsing the Allure Art Center, visiting the Historic Christ Church & Museum, and touring Carters Creek aboard True Love. Don’t miss a unique gourmet experience at the hands of the talented Chef Meseret Crockett at The Dining Hall.

The Hope and Glory Inn, 65 Tavern Road, Irvington, VA 22480, Phone: 804-438-6053

25. Watermen Heritage Tours

Watermen Heritage Tours
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Watermen Heritage Tours honors the watermen of the Chesapeake Bay, who have played an essential role in the history, culture, and economy of the region and have become an endangered Maryland icon. Offering a rare glimpse into their way of life, Watermen Heritage Tours provides authentic and entertaining experiences that celebrate and preserve a rich Chesapeake Bay tradition and give visitors a view of the bay from the perspective of the people who live and work on the water. Commercial fishermen, crabbers, and oystermen have been trained as guides who take visitors out on their vessels to give an inside look at aquafarming, crab shedding, and oyster tonging as it was done in the old day. Customized trips also include beautiful scenery, such as think lighthouses and nature preserves along the way.

716 Giddings Ave #42, Annapolis, MD 21401, Phone: 443-261-2369

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