Discover the Charm of Chestertown Historic District
Explore the rich history and charm of Chestertown Historic District, where every corner tells a story of Maryland's vibrant past.
Nestled in the heart of Maryland, Chestertown Historic District offers a captivating journey through time with its beautifully preserved architecture, historic sites, and vibrant community. Ideal for history enthusiasts and casual visitors alike, this charming district invites exploration and discovery.
A brief summary to Chestertown Historic District
- Chestertown, Maryland, 21620, US
- +1410-778-3499
- Visit website
Local tips
- Visit during the annual Chestertown Tea Party Festival for a lively celebration of the town's history.
- Take a guided walking tour to gain deeper insights into the historical significance of the area.
- Don't miss out on local artisan shops for unique souvenirs and handmade crafts.
- Enjoy a peaceful afternoon by the Chester River, where you can picnic or simply relax by the water.
- Check out the local calendar for events, as there are often art shows and farmers markets happening.
Getting There
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Car
If you're traveling by car, head toward Chestertown, MD 21620. From major highways, take Route 301 or Route 50 to Route 213, which will lead you directly into Chestertown. Upon entering the town, follow signs for the Historic District. Parking is available throughout the district, but be mindful of any parking fees that may apply. The GPS coordinates for the Chestertown Historic District are approximately 39.2082° N, 76.0649° W.
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Public Transportation
For those using public transportation, the Maryland Transit Administration (MTA) offers bus services that can connect you to Chestertown from nearby towns. You can take the MTA Route 201 bus to the Chester River Bridge stop, which is close to the Historic District. From the bus stop, it’s a short walk to the main attractions. Be sure to check the MTA schedule for routes and times, as they may vary. A one-way fare on the bus is typically around $2.
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Bicycle
If you're feeling adventurous, biking is a great way to explore the area. Chestertown has bike-friendly routes. Make your way to the Chester River and follow the scenic trails into the town. There may be bike rental services available in nearby areas, and remember to wear a helmet and follow local biking regulations.
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Walking
Once you arrive in Chestertown, the Historic District is very walkable. You can explore on foot, taking in the charming streets and architecture. Make sure to wear comfortable shoes, as you may want to spend a few hours wandering around and visiting local shops and eateries.
Discover more about Chestertown Historic District
Iconic landmarks you can’t miss
Chestertown Historic District
0.0 km
Explore the rich history and charm of Chestertown Historic District, where every corner tells a story of Maryland's vibrant past.
Eastern Neck Island
24.2 km
Explore the tranquil beauty of Eastern Neck Island, a hidden gem in Maryland, perfect for nature lovers and outdoor adventures.
Gunpowder Falls State Park Hammerman Area bathrooms
29.4 km
Discover the beauty of Gunpowder Falls State Park Hammerman Area with its scenic beach, picnic spots, and abundant recreational activities for all ages.
West Dover Hundred Sign
29.6 km
Explore the West Dover Hundred Sign, a historical landmark in Delaware that showcases the rich cultural heritage and stories of the region's past.
Watermen's Monument
30.8 km
Experience the essence of Chesapeake Bay's fishing heritage at Watermen's Monument, a key historical landmark in Grasonville, Maryland.
Shaw Family Cemetery
31.8 km
Discover the tranquil beauty and historical significance of Shaw Family Cemetery in Edgemere, Maryland, a serene retreat for reflection and exploration.
Historic Craighill Channel Upper Range Front Light Station
33.0 km
Explore the Historic Craighill Channel Upper Range Front Light Station in Edgemere, Maryland, a vital piece of maritime history and stunning coastal views.
Baltimore Harbor Light
33.2 km
Discover the historic Baltimore Harbor Light, a maritime beacon in Chesapeake Bay, steeped in rich history and breathtaking views.
Rumsey Mansion
33.6 km
Discover the historical elegance and timeless charm of Rumsey Mansion in Joppatowne, Maryland, a captivating landmark steeped in rich history.
Hancock’s Resolution Historic Farm Park
33.9 km
Explore the rich history and scenic beauty of Hancock's Resolution Historic Farm Park, a hidden gem in Pasadena, Maryland.
Fort Smallwood Battery Hartshorne
35.9 km
Discover Fort Smallwood Battery Hartshorne, a historic landmark in Pasadena, Maryland, offering breathtaking views and a deep dive into military history.
Wye Island
36.0 km
Experience the natural wonders of Wye Island, a serene escape in Maryland, perfect for outdoor adventures and wildlife observation.
Elk Neck
36.2 km
Discover the tranquil beauty of Elk Neck, Maryland: a serene peninsula offering outdoor adventures, stunning views, and rich wildlife experiences.
Stumpy's Hatchet House-Axe Throwing bar
38.0 km
Discover an exhilarating experience at Stumpy's Hatchet House, where axe throwing meets fun for all ages in Middletown, Delaware.
Putters Paradise
38.5 km
Discover the whimsical world of Putters Paradise, where every hole offers fun and adventure for the whole family in Middletown, Delaware.
Unmissable attractions to see
Queen Anne's Museum-Eastern
20.4 km
Explore the rich history and unique exhibits at Queen Anne's Museum, a hidden gem in Centreville, Maryland.
Mount Harmon Plantation
22.3 km
Explore the historic charm and natural beauty of Mount Harmon Plantation in Maryland, where history and nature intertwine beautifully.
Eastern Neck National Wildlife Refuge
24.0 km
Explore the breathtaking Eastern Neck National Wildlife Refuge in Maryland, a remarkable sanctuary for wildlife and nature lovers alike.
Hart-Miller Island State Park
26.4 km
Explore the natural beauty and diverse wildlife at Hart-Miller Island State Park, a serene retreat in Essex, Maryland, perfect for outdoor adventures.
Delaware Sign
26.8 km
Discover the welcoming spirit of Delaware at the iconic Delaware Sign, a vibrant landmark celebrating the state's rich heritage.
Welcome to Delaware sign
27.2 km
Discover Delaware: A charming introduction to the First State, inviting you to explore its rich history and beautiful landscapes.
Turkey Point Lighthouse
27.3 km
Explore Turkey Point Lighthouse: A stunning historical landmark offering breathtaking views, scenic hiking trails, and nature's tranquility on the Chesapeake Bay.
Deleware Welcome sign
29.1 km
Discover the charm of Delaware at the iconic Welcome Sign, a perfect spot for memorable photos and a warm introduction to the First State.
Gunpowder Falls State Park Hammerman Area
29.6 km
Discover the beauty of Gunpowder Falls State Park's Hammerman Area, a perfect blend of nature, recreation, and relaxation for every traveler.
Old Wye Mill (Mid April - Mid November)
29.7 km
Explore Old Wye Mill, Maryland's historical gem, where the charm of traditional milling meets scenic beauty amidst the serene countryside.
Rocky Point Park and Beach
29.7 km
Experience the serene beauty of Rocky Point Park and Beach, a perfect outdoor oasis for nature lovers in Essex, Maryland.
The Wye Oak Marker
29.9 km
Explore the Wye Oak Marker in Wye Mills, Maryland, a historical landmark celebrating the legacy of America's grandest white oak tree.
Wye Oak State Park
30.0 km
Explore Wye Oak State Park, a serene natural retreat in Maryland, perfect for hiking, wildlife watching, and enjoying the great outdoors.
Chesapeake Heritage & Visitors Center
30.4 km
Explore the Chesapeake Heritage & Visitors Center for an enriching experience of local history and stunning views of the Chesapeake Bay.
Marshy Point Nature Center
30.6 km
Discover the tranquility of Marshy Point Nature Center, a nature preserve with stunning views and rich wildlife along the Gunpowder River in Maryland.
Essential places to dine
Doc's Riverside Grille
17.4 km
Discover delicious American cuisine at Doc's Riverside Grille in Centreville, MD—where comfort meets flavor by the riverside.
Waterman's Crab House
17.5 km
Discover fresh seafood delights at Waterman's Crab House in Rock Hall, MD - where local flavors meet stunning waterfront views.
Bay Shore Steam Pot
18.2 km
Experience authentic Chesapeake Bay seafood at Bay Shore Steam Pot - where fresh flavors meet warm hospitality in Centreville.
The Riverside Grille
29.4 km
Experience mouthwatering American cuisine at The Riverside Grille amidst breathtaking waterfront views in Middle River, Maryland.
Hunter's Seafood and Market
30.1 km
Discover the best seafood experience at Hunter's Seafood and Market in Grasonville - where freshness meets flavor!
Red Eye's Dock Bar
30.4 km
Discover the perfect blend of delicious food, refreshing drinks, and stunning waterfront views at Red Eye's Dock Bar in Grasonville.
Harris Crab House
30.5 km
Experience fresh crab dishes and stunning waterfront views at Harris Crab House - your ultimate seafood destination in Grasonville.
Dock House
30.6 km
Discover Dock House in Chester MD - A Seafood Paradise Offering Fresh Flavors and Stunning Waterfront Views.
The Big Owl
30.8 km
Experience the flavors of Maryland at The Big Owl – your go-to grill in Grasonville offering delicious dishes and warm hospitality.
The Narrows Restaurant
30.8 km
Discover The Narrows Restaurant in Grasonville – where exquisite seafood meets stunning waterfront views on Maryland's Eastern Shore.
Fisherman's Inn Restaurant
30.8 km
Experience the best seafood dining at Fisherman's Inn Restaurant in Grasonville – where freshness meets flavor in every bite.
Fisherman's Crab Deck
30.9 km
Discover delicious seafood at Fisherman's Crab Deck – where fresh catches meet breathtaking waterfront views in Grasonville.
The Jetty
30.9 km
Experience coastal charm at The Jetty in Grasonville—where fresh seafood meets breathtaking waterfront views.
Bridges Restaurant on Kent Narrows
31.0 km
Experience delightful American cuisine at Bridges Restaurant on Kent Narrows with stunning waterfront views perfect for every occasion.
Oliver Beach Inn
31.2 km
Experience culinary delights at Oliver Beach Inn in Middle River, Maryland – where good food meets stunning waterfront views.
Markets, malls and hidden boutiques
The Finishing Touch
0.2 km
Discover creativity at The Finishing Touch, a charming picture frame shop and art gallery in Chestertown, Maryland, perfect for art lovers and gift seekers.
Queenstown Premium Outlets
26.3 km
Discover unbeatable deals and a wide selection of top brands at Queenstown Premium Outlets, Maryland's ultimate shopping destination.
Gunpowder River
27.7 km
Experience the natural beauty and outdoor adventures at Gunpowder River, a serene escape in Maryland's picturesque landscapes.
Gunpowder Falls Archery Range - Free
29.4 km
Join the excitement at Gunpowder Falls Archery Range, a premier destination for archery enthusiasts in a stunning natural setting.
Wye East Outfitters
29.5 km
Discover the thrill of hunting and outdoor adventures at Wye East Outfitters in Queenstown, Maryland, where nature meets excitement.
Maryland Wildlife Heritage Services
29.7 km
Discover Maryland's commitment to wildlife conservation at the Maryland Wildlife Heritage Services, a hub of knowledge and sustainability.
Eastern Bay Trading Co
29.9 km
Explore unique antiques and vintage furniture at Eastern Bay Trading Co, a hidden gem in Grasonville, Maryland, perfect for treasure hunters and decor enthusiasts.
Mill Creek Farms
31.5 km
Explore Mill Creek Farms: A vibrant produce market in Wye Mills, MD, showcasing fresh local produce and artisanal goods.
The Winery
31.5 km
Discover a world of wines and liquors at The Winery in Chester, MD, where expert staff and extensive selections await every visitor.
The Mistress by Night Dreams
32.5 km
Discover a vibrant adult entertainment store in Edgewood, MD, offering costumes, lingerie, and DVDs to spice up your nights.
The Lot
32.8 km
Discover unique treasures at The Lot, a charming variety store in Middle River, MD, perfect for tourists seeking local souvenirs and gifts.
Half Full Gift Boutique
33.2 km
Explore an enchanting selection of local gifts and artisanal products at Half Full Gift Boutique in Stevensville, Maryland.
The Market at the Chesapeake Bay Beach Club
34.1 km
Explore unique gifts and delicious café treats at The Market at the Chesapeake Bay Beach Club, where stunning views meet local charm.
Shore Shop
34.3 km
Visit the Shore Shop in Stevensville, MD for all your convenience needs and local Maryland flavors, right on your travel route.
The Country Store
34.6 km
Discover the heart of Kenton at The Country Store, your go-to destination for local flavors and convenient shopping.
Essential bars & hidden hideouts
Harbor Shack
17.8 km
Discover delectable seafood and vibrant entertainment at Harbor Shack, Rock Hall's premier dining destination with stunning waterfront views.
Signals Restaurant and Deck Bar
23.1 km
Experience the flavors of the Chesapeake Bay at Signals Restaurant and Deck Bar, where fresh seafood meets stunning waterfront views.
Big Truck Farm Brewery
26.4 km
Experience the charm of Big Truck Farm Brewery in Queenstown, MD, where craft beer meets local flavors in a picturesque setting.
Fireside - Beach Grill Plus
26.9 km
Experience the flavors of coastal dining at Fireside - Beach Grill Plus in Earleville, Maryland, where every meal is a delightful adventure.
Annie's Top of The Beach
27.0 km
Discover the delightful flavors of pizza, ice cream, and sandwiches at Annie's Top of The Beach, your perfect seaside dining destination in Earleville, MD.
Ten Eyck Brewing Company
28.0 km
Experience local craft beer and vibrant community spirit at Ten Eyck Brewing Company in Queenstown, MD.
Row Boat Willie's Dock Bar
29.2 km
Experience the charm of Row Boat Willie's Dock Bar, a waterfront haven in Sparrows Point, MD, where great food, drinks, and live music await.
Pour House Pub
31.3 km
Experience the vibrant atmosphere and delicious offerings at Pour House Pub, Chester's favorite spot for food and fun.
Adams Grille & Tap House Kent Island
31.3 km
Experience mouthwatering barbecue and a vibrant atmosphere at Adams Grille & Tap House on Kent Island, a culinary gem for all food lovers.
Sunset Cove
31.6 km
Experience the serene beauty and delicious flavors of Sunset Cove, a premier American restaurant and bar in Bowleys Quarters, Maryland.
Crazy Tuna Bar & Grille
33.7 km
Experience fresh seafood and vibrant nightlife at Crazy Tuna Bar & Grille in Essex, Maryland – a must-visit waterfront destination for food lovers.
Tiki Lee’s Dock Bar
33.9 km
Experience the vibrant atmosphere and delicious seafood at Tiki Lee's Dock Bar, a must-visit waterfront destination in Sparrows Point, Maryland.
Bushmill Tavern
34.1 km
Discover the vibrant flavors and welcoming atmosphere of Bushmill Tavern, a top dining destination in Abingdon, Maryland.
Parrot Bar
35.1 km
Experience the lively charm of Parrot Bar in Chester, MD—where delicious grilled dishes meet a vibrant social atmosphere.
Brewers Landing
35.7 km
Experience the best of American cuisine at Brewers Landing, a lively grill and sports bar in Essex, Maryland, perfect for food lovers and sports fans alike.
