• 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.
  • 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.
  • 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.
  • 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.

Academy Art Museum

Academy Art Museum

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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.
  • When was the museum founded?
    • The museum was founded in 1958 to enhance the appreciation of the arts and culture of the Eastern Shore.
  • 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
  • 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
  • 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).


Adkins Arboretum

Adkins Arboretum

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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.
  • 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.
  • 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
  • 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.
  • 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.


American Cruise Lines

American Cruise Lines

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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.
  • 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
  • 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.
  • 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
  • What is the contact information for American Cruise Lines?
    • Phone: 800-460-4518

American Chestnut Land Trust

American Chestnut Land Trust

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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.
  • What recreational activities are available?
    • Visitors can enjoy 22 miles of trails for:
    • Hiking
    • Mountain biking
    • Horseback riding
  • 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.
  • 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.
  • 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).


Annapolis Yacht Club

Annapolis Yacht Club

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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.
  • Where is the Annapolis Yacht Club located?
    • The club is set on the banks of Spa Creek in Annapolis Harbor.
  • 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
  • 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.
  • What is the contact information for the Annapolis Yacht Club?
    • 2 Compromise St, Annapolis, MD 21401
    • Phone: 410-263-9279

C&D Canal Museum

C&D Canal Museum

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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.
  • Who owns and operates the C&D Canal Museum?
    • The museum is owned and operated by the U.S. Army Corps of Engineers.
  • 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.
  • 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.
  • What is the contact information for the C&D Canal Museum?
    • Address: 815 Bethel Rd, Chesapeake City, MD 21915
    • Phone: 410-885-5622

Calvert Cliffs State Park

Calvert Cliffs State Park

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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.
  • 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.
  • 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.
  • 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.
  • What is the contact information for Calvert Cliffs State Park?
    • Address: 10540 HG Trueman Rd, Lusby, MD 20657
    • Phone: 443-975-4360

Captain John Smith Chesapeake National Historic Trail

Captain John Smith Chesapeake National Historic Trail

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  • What is the Captain John Smith Chesapeake National Historic Trail?
  • 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.
  • 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.
  • 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.
  • What is the contact information for the Captain John Smith Chesapeake National Historic Trail?
    • Location: Yorktown, VA 23690
    • Phone: 757-898-3400

Chesapeake Bay Maritime Museum

Chesapeake Bay Maritime Museum

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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.
  • What types of watercraft are in the museum's collection?
    • The collection includes drake-tail oyster boats, log canoes, and skipjacks.
  • What is the history of the museum site?
    • The museum is located on a site that once housed seafood packing warehouses and workboats.
  • 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.
  • 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
  • What is the contact information for the Chesapeake Bay Maritime Museum?
    • Address: 213 N Talbot St, St. Michaels, MD 21663
    • Phone: 410-745-2916

Chesapeake Wine Trail

Chesapeake Wine Trail

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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.
  • Which regions does the Chesapeake Wine Trail cover?
    • The trail encompasses the Northern Neck and Middle Peninsula of Virginia.
  • 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
  • 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
  • What is the contact information for the Chesapeake Wine Trail?
    • Address: Caret Cellars, 495 Meadow Landing Lane, Caret, VA 22436
    • Phone: 540-413-6454


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.

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