Ready for a coastal escape rich in seafood, sailing, and scenic views? Explore Chesapeake Bay! From quaint towns to historic lighthouses, Maryland’s Chesapeake Bay region offers fresh crab feasts, waterfront adventures, and a deep connection to American maritime history.
Best Time to Visit
The best time to visit Chesapeake Bay is from late spring through early fall (May to October). This is prime season for boating, seafood festivals, and soaking up warm bay breezes.
How to Get There
- By Car: Chesapeake Bay is accessible via U.S. Route 50 and I-95, with key destinations like Annapolis, St. Michaels, and Cambridge within 1–2 hours of Baltimore and Washington, D.C.
- By Air: Baltimore/Washington International Airport (BWI) is the closest major airport to the western shore; Salisbury Regional Airport serves the Eastern Shore.
- By Boat: Popular with boaters—many marinas and water taxis connect towns along the bay.
Where to Stay
- Inn at Perry Cabin (St. Michaels) – Luxurious waterfront resort with spa services and sailing lessons.
- Tilghman Island Inn – Romantic boutique hotel with sunset views and gourmet dining.
- Hyatt Regency Chesapeake Bay (Cambridge) – Family-friendly resort with golf, pools, and marina access.
Top Attractions
⮕ Unleash Your Inner Creative at the Academy Art Museum
Brush up on fine art where tradition meets modern expression.
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What is the Academy Art Museum?
- The Academy Art Museum is located in Easton, Maryland.
- It is housed in a beautifully preserved early 19th-century schoolhouse.
- The museum features a permanent and rotating collection of artworks from local and national artists.
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When was the museum founded?
- The museum was founded in 1958 to enhance the appreciation of the arts and culture of the Eastern Shore.
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What type of art collections does the museum feature?
- The museum’s permanent collection includes works by both local and international artists.
- It houses works on paper by modern American and European masters.
- The collection also includes significant photographs, prints, and drawings by prominent individuals such as:
- Robert Rauschenberg
- Pierre Bonnard
- Martin Puryear
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Does the museum offer cultural and educational programs?
- Yes! The museum provides a broad spectrum of cultural and educational offerings.
- It hosts visual and performing arts classes for both adults and children.
- Other programs include:
- Lecture series
- Concerts
- Dance performances
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What is the contact information for the Academy Art Museum?
- 106 South St, Easton, MD 21601
- Phone: 410-822-2787
Easton, MD is 1.5 hour weekend getaway from Baltimore (64.9 miles via US-301 N/US-50 E and US-50 E/Ocean Gateway).
⮕ Wander Wild at Adkins Arboretum
Hike, breathe, and reconnect with native landscapes.
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What is Adkins Arboretum?
- The Adkins Arboretum is a 400-acre native garden and preserve located in Tuckahoe State Park, Ridgely, Maryland.
- It features a living collection of more than 600 native plant species.
- The arboretum includes over five miles of meadow and woodland paths.
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What is the mission of Adkins Arboretum?
- The arboretum was established to promote the appreciation and conservation of native plants in the Chesapeake Bay region.
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What educational programs and activities does the arboretum offer?
- Visitors can participate in a variety of educational programs, including:
- Guided walks
- Demonstrations
- Lectures
- Art exhibitions
- Seasonal community events
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Does the arboretum have a shop?
- Yes! The arboretum features a gift and book shop.
- Visitors can also purchase native plants featured in the garden.
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What is the contact information for Adkins Arboretum?
- 12610 Eveland Rd, Ridgely, MD 21660
- Phone: 410-634-2847
You can reach the town of Ridgely, MD in 1.5 hours from Baltimore (64.0 miles via US-301 N/US-50 E), perfect for a day trip.
⮕ Cruise Like a Local with American Cruise Lines
Sail past history and hospitality on Chesapeake waters.
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What is American Cruise Lines?
- American Cruise Lines is a small-ship cruise line operating in the United States.
- The company runs twelve small cruise ships and riverboats, offering an authentic All-American experience.
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Where does American Cruise Lines operate?
- American Cruise Lines sails along:
- The Eastern Seaboard
- The Western Seaboard
- The Mississippi-Ohio River system
- The Columbia-Snake River system
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What makes American Cruise Lines unique?
- The fleet consists of the newest and most environmentally-friendly small cruise ships in the country.
- They offer a personalized and luxurious experience for their guests.
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What services does American Cruise Lines provide?
- Guests enjoy a range of world-class services, including:
- Award-winning cuisine and fine wines
- Beautiful accommodations with high-end amenities
- Daily entertainment, from lectures to live music
- Highly personalized service and hospitality
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What is the contact information for American Cruise Lines?
⮕ Get Grounded with the American Chestnut Land Trust
Protect forests and hike trails where restoration thrives.
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What is the American Chestnut Land Trust?
- The American Chestnut Land Trust protects 3,000 acres of natural landscapes in Calvert County, Maryland.
- The area includes farmlands, wetlands, and dense hardwood forests.
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What recreational activities are available?
- Visitors can enjoy 22 miles of trails for:
- Hiking
- Mountain biking
- Horseback riding
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Where is the American Chestnut Land Trust located?
- The preserve is located in Calvert County, Maryland, about an hour’s drive from Washington, D.C.
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What special features does the preserve have?
- The area includes several historic structures and interpretive trails.
- It also features a community farm and offers guided canoe trips.
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What are the hiking trails like?
- The southern section of the preserve has four primary hiking trail loops that are daisy-chained together.
- These trails offer excellent hikes of varying lengths, suitable for all levels of hikers.
676 Double Oak Rd, Prince Frederick, Maryland 20678, Phone: 410-414-3400
You can reach American Chestnut Land Trust on a 2-hour weekend getaway from D.C. (44.8 miles via MD-4 S and MD-4 S).
⮕ Raise the Sails at Annapolis Yacht Club
Navigate prestige and performance on historic waters.
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What is the Annapolis Yacht Club?
- The Annapolis Yacht Club is a premier private yacht club founded in 1886.
- It provides a wide range of quality services for club members.
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Where is the Annapolis Yacht Club located?
- The club is set on the banks of Spa Creek in Annapolis Harbor.
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What services and activities does the club offer?
- Originally a canoe club, it has grown into a world-class yacht club offering:
- Sailboat racing
- A vigorous junior sailing program
- Cruising for sailors and powerboaters
- Fun and educational winter activities
- First-class dining and banquet facilities
- Social events throughout the year
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What dining options are available?
- The clubhouse features a beautifully appointed dining room.
- Members can enjoy award-winning cuisine and fine wines from around the world.
- The dining experience includes spectacular harbor views.
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What is the contact information for the Annapolis Yacht Club?
- 2 Compromise St, Annapolis, MD 21401
- Phone: 410-263-9279
⮕ Unlock Canal Secrets at the C&D Canal Museum
Discover the gritty ingenuity that moved America forward.
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What is the C&D Canal Museum?
- The C&D Canal Museum explores the history of the 14-mile-long C&D Canal.
- The canal was built in the 19th century to connect Delaware Bay and the Chesapeake Bay.
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Who owns and operates the C&D Canal Museum?
- The museum is owned and operated by the U.S. Army Corps of Engineers.
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What can visitors expect to see at the museum?
- The museum showcases the history of the world’s third busiest shipping canal.
- Visitors can explore interactive displays, watch fascinating videos, and view exciting exhibits about the building of the canal.
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Where is the museum located?
- The museum is housed in the original pump house, which dates back to the 18th century.
- The pump house was used to control water levels in the locks of the first canal.
- The building is listed on the National Register of Historic Places.
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What is the contact information for the C&D Canal Museum?
- Address: 815 Bethel Rd, Chesapeake City, MD 21915
- Phone: 410-885-5622
⮕ Dig Deep at Calvert Cliffs State Park
Hunt fossils and bask in coastal serenity.
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What is Calvert Cliffs State Park?
- Calvert Cliffs State Park is a public reserve and recreation area located in Lusby, Maryland.
- The park protects and preserves the Calvert Cliffs, where over 600 species of fossils from the Miocene era have been discovered.
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Where are the Calvert Cliffs located?
- The cliffs extend for 24 miles along the eastern flank of the Calvert Peninsula.
- The area was once submerged beneath a shallow sea and is now a treasure chest of prehistoric gems, including ancient sharks’ teeth and oyster shells.
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How old are the Calvert Cliffs?
- The cliffs were formed over 20 million years ago.
- They reveal the remains of prehistoric species, including enormous rays, seabirds, whales, and sharks.
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What recreational activities does the park offer?
- The park has a lovely sandy beach, a recycled tire playground, and freshwater and tidal marshlands.
- There are over 13 miles of hiking trails.
- Visitors can enjoy fishing, swimming, and beachcombing.
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What is the contact information for Calvert Cliffs State Park?
- Address: 10540 HG Trueman Rd, Lusby, MD 20657
- Phone: 443-975-4360
⮕ Paddle Through Time on the Captain John Smith Trail
Trace history by kayak on this National Historic route.
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What is the Captain John Smith Chesapeake National Historic Trail?
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When did John Smith and his crew explore the Chesapeake?
- Their journey took place between 1607 and 1609.
- They mapped and documented nearly 3,000 miles of the Bay and its rivers.
- The team visited thriving Native American communities and gathered information about the land.
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How long is the Captain John Smith Chesapeake National Historic Trail?
- The trail extends for around 3,000 miles along the Chesapeake Bay and its tributaries.
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When was the trail designated as a National Historic Trail?
- The trail was officially designated as a National Historic Trail in 2006.
- It is the first national water trail of its kind.
- It is also one of only two National Historic Trails.
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What is the contact information for the Captain John Smith Chesapeake National Historic Trail?
- Location: Yorktown, VA 23690
- Phone: 757-898-3400
⮕ Anchor Your Curiosity at the Chesapeake Bay Maritime Museum
Explore shipbuilding, oysters, and Chesapeake traditions.
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What is the Chesapeake Bay Maritime Museum?
- The Chesapeake Bay Maritime Museum is located in the Eastern Shore town of St. Michaels.
- The museum celebrates maritime history and houses the largest collection of historic Chesapeake Bay watercraft.
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What types of watercraft are in the museum's collection?
- The collection includes drake-tail oyster boats, log canoes, and skipjacks.
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What is the history of the museum site?
- The museum is located on a site that once housed seafood packing warehouses and workboats.
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Does the museum have a working boatyard?
- Yes, the museum features a working boatyard where historic wooden boats are lovingly restored.
- Visitors can apprentice with a shipwright to learn the trade hands-on.
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What other attractions does the museum offer?
- A beautiful old lighthouse
- A butterfly garden
- A variety of exhibits highlighting the Bay’s history
- A living shoreline
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What is the contact information for the Chesapeake Bay Maritime Museum?
- Address: 213 N Talbot St, St. Michaels, MD 21663
- Phone: 410-745-2916
⮕ Sip and Savor Along the Chesapeake Wine Trail
Toast Maryland’s terroir one glass at a time.
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What is the Chesapeake Wine Trail?
- The Chesapeake Wine Trail is a wine-lovers trail that winds through Virginia’s Chesapeake Bay wine region.
- The trail features nine wineries offering tastings and tours.
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Which regions does the Chesapeake Wine Trail cover?
- The trail encompasses the Northern Neck and Middle Peninsula of Virginia.
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Which wineries are included in the trail?
- Caret Cellars
- General’s Ridge Vineyard
- Good Luck Cellars
- Ingleside Vineyards
- Jacey Vineyards
- The Dog and Oyster
- Vault Field Vineyards
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What experiences can visitors enjoy on the trail?
- Guided tours of the wineries
- Wine tastings featuring top vintages
- Pairings with local farm-to-table fare
- Enjoying wine in beautiful scenic settings
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What is the contact information for the Chesapeake Wine Trail?
- Address: Caret Cellars, 495 Meadow Landing Lane, Caret, VA 22436
- Phone: 540-413-6454
More Local Attractions
- Blackwater National Wildlife Refuge – Spot bald eagles and paddling trails in this stunning Eastern Shore preserve.
- Annapolis Historic District – Stroll cobblestone streets, tour the U.S. Naval Academy, and shop in Maryland’s capital.
- Chesapeake Bay Bridge – Iconic 4.3-mile bridge offering sweeping views of the bay.
- Hoopers Island – Remote and scenic destination for oyster tasting, crab shacks, and bayfront sunsets.
Where to Eat
- Crab Claw Restaurant (St. Michaels) – Waterfront spot for blue crabs, hush puppies, and classic bay views.
- Suicide Bridge Restaurant (Hurlock) – A local favorite for fresh crab cakes, seafood platters, and river cruises.
- Boatyard Bar & Grill (Annapolis) – Nautical-themed eatery known for oysters, mahi tacos, and local beer.
Local Events
- Maryland Seafood Festival (September, Annapolis) – A celebration of Chesapeake cuisine with live music and crab soup cook-offs.
- St. Michaels WineFest (April) – Sample local and international wines across charming venues in town.
- Waterfowl Festival (November, Easton) – Three-day event featuring art, heritage, and sporting traditions of the bay.
Day Trips Within 30 Minutes of Chesapeake Bay, Maryland
- Annapolis (10–15 min) – Stroll historic streets, tour the U.S. Naval Academy, and dine along the scenic harborfront.
- Edgewater (10–15 min) – Launch a kayak, visit Quiet Waters Park, or enjoy casual waterfront dining.
- Stevensville (20–25 min) – Cross the Bay Bridge to shop local boutiques, relax by the water, or bike the Cross Island Trail.
- Chester (25–30 min) – Explore Chesapeake farms, sip local wines, or fish from marinas on Kent Island.
- Deale (25–30 min) – Visit peaceful marinas, grab seafood at dockside restaurants, or explore small-town charm.
- Shady Side (25–30 min) – Relax in waterfront parks, visit the Captain Avery Museum, or enjoy quiet Chesapeake views.
- Galesville (20–25 min) – Paddle the West River, explore historic buildings, or dine at quaint bayside cafés.
- Mayo (15–20 min) – Lounge on Beverly Triton Beach or take a sunset cruise on the bay.
- Riva (10–15 min) – Access local marinas, enjoy riverside scenery, and experience a laid-back boating community.
FAQ
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What is Chesapeake known for?
- The City of Chesapeake and the Chesapeake Bay estuary are filled with natural beauty and historical significance.
- The area is known for its stunning scenery and rich cultural heritage.
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What kind of waterways are in Chesapeake?
- Chesapeake is home to over 20 miles of waterways, canals, lakes, and rivers.
- Visitors can enjoy activities like boating, kayaking, and fishing.
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Are there parks and outdoor recreation areas in Chesapeake?
- Yes! Chesapeake has several parks and outdoor spaces perfect for recreation.
- Popular outdoor activities include:
- Mountain biking on scenic trails.
- Horseback riding through natural landscapes.
- Picnicking in beautiful parks.
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What cultural attractions can visitors explore?
- Chesapeake offers a variety of galleries, museums, and restaurants.
- Visitors can explore local history and art while enjoying the region’s unique charm.
At a Glance
Best Time to Visit |
Places to Stay |
Tips for Visiting |
Spring (March-May) – Pleasant weather ideal for sailing, fishing, and waterfront activities. |
Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina – Luxury waterfront resort in Cambridge. |
Explore Annapolis Historic District – Enjoy shops, cafés, and historic landmarks. |
Summer (June-August) – Warm temperatures perfect for boating, beaches, and seafood festivals. |
The Inn at Perry Cabin (St. Michaels) – Elegant accommodations with stunning bay views. |
Visit Sandy Point State Park – Relax at the beach, swim, or picnic by the bay. |
Fall (September-November) – Mild weather and fewer crowds, ideal for scenic drives and seafood dining. |
Harbourtowne Resort (St. Michaels) – Comfortable lodging overlooking the bay. |
Attend OysterFest – Celebrate Maryland seafood traditions and culture. |
Winter (December-February) – Quiet charm, ideal for cozy stays, wildlife watching, and historical visits. |
Robert Morris Inn (Oxford) – Historic inn offering cozy winter stays. |
Explore Blackwater National Wildlife Refuge – Discover winter bird migrations and serene landscapes. |
Map:
Plan Your Trip