Chestertown, Maryland
Exploring the Charms of Chestertown, Maryland
Welcome to Chestertown, a hidden gem nestled on the banks of the Chester River in Maryland! This picturesque town is renowned for its rich history, stunning waterfront, and vibrant arts scene. Over the course of our three-day weekend trip, we’ll dive into Chestertown’s fascinating past, indulge in mouthwatering cuisine, and soak up the beauty of its surroundings. So, let’s get started on an unforgettable adventure!
Day 1: Unveiling the Historic Treasures
Morning: Strolling Through Historic District
Begin your journey by immersing yourself in Chestertown’s storied past. Take a leisurely stroll through the town’s Historic District, lined with well-preserved 18th-century homes. Admire the architectural marvels, such as the Geddes-Piper House and the White Swan Tavern. Don’t miss the famed Schooner Sultana, a replica of an 18th-century ship, where you can learn about local maritime history.
Lunch: Relishing Chesapeake Bay Delights
For a true taste of the region, head to The Fish Whistle at the Granary. This waterfront eatery offers panoramic views of the Chester River while serving up delectable seafood dishes. Savor the Chesapeake Bay delicacies like crab cakes or locally caught rockfish, paired perfectly with a refreshing craft beer or a glass of wine.
Afternoon: Art and Culture Exploration
Indulge your artistic side by visiting the RiverArts Gallery, showcasing a diverse array of local and regional artwork. From paintings and sculptures to ceramics and jewelry, you’ll discover the talents of Chesapeake Bay’s creative community. If you’re lucky, catch a live performance or exhibition at the Garfield Center for the Arts, a vibrant cultural hub in town.
Dinner: Culinary Delights in a Quaint Setting
For an intimate dining experience, head to the Lemon Leaf Café. Located in a charming 18th-century building, this restaurant offers a fusion of international flavors using locally sourced ingredients. Treat your taste buds to their mouthwatering specials, such as the Thai basil chicken or the Chesapeake seafood pasta.
Evening: Sunset Cruise on the Chester River
End your day with a breathtaking sunset cruise along the Chester River aboard the Chester River Packet. Sail past scenic landscapes, including lush shores and charming waterfront homes, as you soak in the natural beauty of the area. Don’t forget your camera to capture the vibrant hues painting the sky.
Day 2: Embracing Outdoor Adventures
Morning: Exploring Wilmer Park
Start your day at the scenic Wilmer Park, a perfect spot for a morning picnic or a peaceful stroll. This riverfront park offers breathtaking views of the Chester River and features walking trails, picnic tables, and a playground. Take a moment to bask in the tranquility of the surroundings before your action-packed day.
Lunch: Farm-to-Table Dining Experience
Satisfy your hunger at Evergrain Bread Company, a charming bakery and café committed to using locally grown ingredients. Indulge in their artisan breads, homemade soups, and farm-fresh salads. For a delightful treat, try their famous avocado toast or a delectable pastry from their irresistible selection.
Afternoon: Kayaking on the Chester River
Get ready for an exciting adventure on the water as you kayak along the Chester River. Rent kayaks from Chester River Kayak Adventures and paddle your way through stunning landscapes, observing the diverse wildlife and the serenity of the river. It’s an excellent opportunity to connect with nature and experience the beauty of the Chesapeake Bay region.
Dinner: Rustic Elegance with a Waterfront View
Dine at the charming 98 Cannon Riverfront Grille, offering a rustic yet refined atmosphere with picturesque views of the Chester River. Their menu features a delightful fusion of American and Mediterranean flavors, ranging from fresh seafood to succulent steaks. Be sure to try their signature dish, the Chesapeake crab macaroni and cheese.
Evening: Ghost Walk through Historic Chestertown
Prepare for a spine-tingling evening as you join the Historic Ghost Walk of Chestertown. Led by knowledgeable guides, this tour takes you on a lantern-lit journey through the town’s haunted history. Listen to captivating tales of ghostly encounters and legends intertwined with Chestertown’s past. It’s a unique and eerie way to end your day.
Day 3: Discovering Natural Beauty
Morning: Visiting Chesapeake Farms
Embark on a scenic drive to Chesapeake Farms, a sprawling estate boasting an enchanting blend of nature and agriculture. Explore the vast grounds, adorned with picturesque landscapes, manicured gardens, and charming farmhouses. Enjoy a leisurely walk or bike ride along the nature trails, absorbing the serenity and beauty of this idyllic retreat.
Lunch: Waterside Dining at the Blue Heron Café
Pause for lunch at the Blue Heron Café, a waterfront eatery that combines exceptional cuisine with breathtaking views of the Chester River. Savor their delectable menu, featuring dishes crafted from the freshest local ingredients. From their crab bisque to their Chesapeake-inspired sandwiches, every bite is a celebration of Chesapeake Bay flavors.
Afternoon: Wildlife Adventure at Eastern Neck National Wildlife Refuge
Spend your afternoon exploring the picturesque Eastern Neck National Wildlife Refuge. This natural paradise is home to a diverse array of wildlife and offers numerous trails for hiking and birdwatching. Marvel at the sight of majestic bald eagles, catch glimpses of migratory birds, and enjoy the serenity of the tidal marshes and woodlands.
Dinner: Farm-to-Table Fare at Luisa’s Cucina Italiana
Delight your palate with a farm-to-table Italian feast at Luisa’s Cucina Italiana. This cozy restaurant takes pride in using local and organic ingredients to create authentic Italian dishes bursting with flavors. Indulge in their homemade pasta, wood-fired pizzas, and mouthwatering desserts. Don’t forget to pair your meal with a fine Italian wine.
Evening: Sunset at Betterton Beach
As your trip comes to a close, head to Betterton Beach to witness a spectacular Chesapeake Bay sunset. Sink your toes into the soft sand, breathe in the salty sea air, and marvel at the vibrant colors as the sun bids farewell to the horizon. It’s a serene and magical moment that will leave you with lasting memories.
With its rich history, captivating scenery, and warm hospitality, Chestertown offers an unforgettable getaway. So pack your bags, gather your friends, and embark on a weekend full of adventure and discovery in this charming Maryland town. Chestertown awaits your arrival!
*Note: Please check attraction websites for the most up-to-date information on opening hours, reservations, and any restrictions or guidelines due to COVID-19.