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Chestertown

Nestled along the scenic Chester River, Chestertown, Maryland, is a charming small town that captures the essence of historic Eastern Shore living. Known for its beautifully preserved colonial architecture, brick-lined streets, and welcoming riverfront, Chestertown offers visitors a unique blend of history, culture, and small-town hospitality. The town is famous for its vibrant arts scene, from local galleries and theaters to live music and festivals that celebrate creativity year-round.

Featured Trip Itineraries

What to Do in Chestertown, Maryland

Recommendations

Landmark4.6/5

Washington College

Located in Chestertown, Maryland, Washington College is a hidden gem for intellectuals and culture enthusiasts. With its stunning campus on the banks of the Chester River, this liberal arts college offers a diverse and vibrant community. Embrace your inner bookworm in its historic library or enjoy outdoorsy activities in its sprawling green spaces. Don't forget to take a selfie next to its iconic statue of George Washington!

Culture4.7/5

Chestertown Historic District

Welcome to Chestertown Historic District! This delightful gem in Maryland takes you on a captivating journey through time. Marvel at beautifully preserved 18th-century houses, explore charming brick-lined streets, and soak up the captivating history. Don't miss the picturesque waterfront and indulge in local eats. Whether you're a history buff or just looking for a charming escape, Chestertown has got you covered!

Shop4.7/5

Chestertown Farmers Market

The vibrant Chestertown Farmers Market on 118 N Cross St in Chestertown, MD transports you to a delicious wonderland of fresh produce, tantalizing treats, and lively chatter. Indulge in the colorful array of locally-grown goodies, from juicy heirloom tomatoes to artisanal cheeses. Don't forget to strike up a chat with the friendly vendors and snag some quirky souvenirs from local artisans. A tasty adventure awaits!

Landmark4.6/5

Chestertown Marina LLC

Welcome to Chestertown Marina LLC, the perfect spot to dock your boat and enjoy the charming town of Chestertown, MD. Located at 207 S Water St unit a, our marina offers a prime location for exploring the breathtaking Chesapeake Bay. With top-notch facilities, friendly staff, and easy access to local attractions, we promise an unforgettable boating experience. So, grab your captain's hat and set sail for adventure!

Culture4.6/5

Emmanuel Episcopal Church

Welcome to Emmanuel Episcopal Church in the charming town of Chestertown, MD! This historic gem on 101 N Cross St is bursting with beauty and spirituality. Marvel at the stunning architecture, admire the intricate stained glass windows, and soak in the peaceful ambiance. Whether you're seeking a moment of tranquility or a dose of local history, this is the spot for you!

Outdoor4.6/5

Wilmer Park

Welcome to Wilmer Park, a hidden gem in Chestertown, MD. This charming waterfront park is the perfect retreat for nature lovers and adventure seekers alike. With lush greenery, scenic walking trails, and stunning views of the Chester River, it's a paradise for picnics and serene strolls. Don't forget your camera, as you'll want to capture the enchanting sunsets and playful wildlife that call this park their home.

Attraction

Chestertown Station

Welcome to Chestertown Station! Located at 405-391 S Cross St in charming Chestertown, MD, this lively hub invites travelers to explore the delightful town. Marvel at the historic architecture, soak up the vibrant arts scene, and enjoy mouthwatering local cuisine. With easy access to all the town's attractions, Chestertown Station is your ticket to an unforgettable adventure!

Outdoor4.5/5

Chester River

Nestled in the heart of the Chesapeake region, Chester River boasts stunning views, rich history, and vibrant wildlife, making it an ideal spot for boating, fishing, and enjoying the serene beauty of Maryland's waterways.

Culture4.8/5

Sumner Hall

Sumner Hall, a historic landmark in Chestertown, MD, showcases remarkable architectural beauty and serves as a vibrant hub for cultural events, making it a must-visit stop for those exploring the region's rich heritage.

Outdoor4.5/5

Chester River Yacht & Country Club

Nestled along the scenic Chester River, the Chester River Yacht & Country Club offers stunning waterfront views, vibrant social events, and exceptional golf, making it a beloved destination for relaxation and recreation in Chestertown.

Attraction5/5

Piney Grove

Piney Grove, nestled in Chestertown, MD, is an iconic retreat known for its serene landscapes and rich history, making it a perfect destination for nature lovers and history enthusiasts alike.

Eat4.2/5

The Kitchen at the Imperial

Step into The Kitchen at the Imperial and let your taste buds embark on a culinary adventure. Located at 208 High St in Chestertown, MD, this vibrant eatery invites you to indulge in a playful feast of delectable dishes. From hearty breakfasts to creative lunches, their menu promises to satisfy any foodie's cravings. Get ready to fill your belly and make delicious memories!

Drink$4.4/5

Blue Bird Tavern

Located in the charming town of Chestertown, Blue Bird Tavern is a must-visit spot for every traveler. This funky tavern boasts a vibrant atmosphere, fantastic cocktails, and a menu that will leave your taste buds dancing. Whether you're in the mood for a classic burger or some mouthwatering seafood, Blue Bird Tavern has got you covered. Don't miss out on this quirky gem!

Eat$$$4.6/5

Evergrain Bread Company

Calling all bread lovers! Evergrain Bread Company is a hidden gem nestled on 201 High St, Chestertown, MD. Prepare for a delightful adventure as you indulge in their artisanal bread, baked fresh daily. From crusty baguettes to fluffy croissants, their heavenly creations will transport your taste buds to absolute bliss. Grab a loaf (or two) and explore the flavors of this quaint town!

Cafe$$4.3/5

Play It Again Sam

Welcome to Play It Again Sam in Chestertown, MD! This treasure trove of music delights awaits you with its eclectic collection of vinyl records, CDs, and cassettes. Get ready to groove to your heart's content as you browse through this musical wonderland. From classic jazz to rock 'n' roll, there's something here for every avid traveler seeking melodies. Don't miss the chance to immerse yourself in the rhythm of this unique spot!

Eat$$4.6/5

Phat Daddy's

Looking for a lip-smacking feast in Chestertown? Phat Daddy's is the ultimate food haven! This funky joint on 205 Spring Ave serves up finger-licking BBQ classics, from tender ribs to juicy pulled pork. Take a break from your journey and dive into their irresistible dishes. Guaranteed to leave your taste buds dancing and your belly grinning! Don't miss this tasty treasure in Chestertown, Maryland.

Eat4.5/5

BAD Alfred's Distilling

Welcome to BAD Alfred's Distilling, the quirkiest spot on High St! Get ready for an adventure as you sample their wickedly delicious craft spirits. From their tantalizing whiskey blends to their dangerously smooth moonshine, BAD Alfred's will make your taste buds dance. Don't miss their lively events and funky decor! Cheers to a wild time in Chestertown, Maryland!

Stays

Stay4.5/5

Brampton 1860

Looking for a cozy retreat in Chestertown? Look no further than Brampton Bed and Breakfast Inn! Nestled on Chestertown Road, this charming inn offers a vibrant ambiance and comfortable rooms. From picturesque gardens to delicious homemade breakfasts, this traveler's haven is the perfect place to unwind. Don't miss the opportunity to soak in the warmth of Brampton's hospitality!

Stay2.75/5

Driftwood Inn

Looking for a coastal escape? Look no further than Driftwood Inn! Located on 609 Washington Ave, Chestertown, MD, this charming spot offers cozy accommodations and a laid-back atmosphere. With stunning views of the water, you'll feel a million miles away from the hustle and bustle. Plus, it's just a short stroll from local shops and dining options. Pack your flip flops and dive into relaxation at Driftwood Inn!

Stay5/5

The Guesthouse Bed and Breakfast

Nestled in the heart of Chestertown, The Guesthouse Bed and Breakfast offers charming accommodations with historic character, delectable breakfast options, and a beautiful garden, making it a perfect retreat for relaxation and exploration.

Stay4.9/5

Inn at Mitchell House

Welcome to the charming Inn at Mitchell House in Chestertown, MD! This historic bed and breakfast offers a delightful escape for weary wanderers. With its picturesque surroundings and cozy rooms, this hidden gem is the perfect spot to recharge. Don't miss out on the scrumptious breakfast served each morning. Prepare for a whimsical stay filled with relaxation and adventure.

Stay4.9/5

White Swan Tavern

Nestled in the heart of Chestertown, White Swan Tavern charms visitors with its cozy vibe and historic flair. Dating back to the 18th century, this picturesque inn offers comfortable rooms for adventurers seeking a touch of nostalgia. Immerse yourself in the town's rich history, explore the nearby waterfront, and savor mouthwatering dishes at the on-site restaurant. A delightful hideaway for time-travelers in search of unforgettable experiences.

Stay4.8/5

Great Oak Manor

Welcome to Great Oak Manor, a charming bed and breakfast nestled on the shores of Chesapeake Bay in Chestertown, Maryland. Immerse yourself in breathtaking views and personalized hospitality. With elegantly appointed rooms, delicious breakfasts, and beach access, your stay will be a dream come true. Discover hidden gems, explore historic Chestertown, and indulge in endless relaxation at this waterfront oasis.

Things To Do
Provided by

4.6/5

45 mins

45-Minute Sea Rocket Speed Boat & Dolphin Cruise in Ocean City MD

The Sea Rocket has been cruising the coast of Ocean City, Maryland for nearly 30 years! Departing from downtown OCMD on Dorchester Street, we will cruise out of the Ocean City Inlet and head up the coast! There are plenty of beautiful sights along the coast as well as wildlife to see! We are always on the lookout for the Atlantic Bottlenose Dolphin! YOU MUST ARRIVE 25 MINUTES EARLY TO YOUR RESERVATION! THE BOAT LEAVES EXACTLY AT THE TIME OF THE TRIP AND DOES NOT WAIT FOR ANYONE WHO IS LATE, SO PLAN ACCORDINGLY!

$39.99

4.5/5

1 h 15 mins

Montgomery Indoor Skydiving Experience with 2 Flights & Personalized Certificate

Feel the thrill of skydiving without jumping out of an airplane. It's true! Head to iFLY Montgomery, a premier indoor skydiving facility powered by a state-of-the-art vertical wind tunnel. After a training session, you'll experience free-fall conditions with the help of an instructor. No experience is necessary, and afterward, you can take home a personalized flight certificate.

$101.00

4.6/5

2 h

A Walking Tour of Frederick, Maryland - The Crossroads of Maryland

I’m Don Burgess, a Frederick resident interested in sharing my passion for heritage tourism and historic preservation as they contribute to preserving and creating a city’s “Sense of Place.” I’ve been a history buff of this region for years, and my role on Facebook as Frederick Tour enables me to combine my love of things old with my skills with things new. I’m a semi-professional photographer who has photographed, shown, and sold images of Frederick, Harpers Ferry, and other regions. See more details about tour in itinerary below and at fredericktour.org We can give tours year round. If it is raining/snowing (light) and you still want to take the tour, we can do that. If it is raining/snowing (hard), we can do a virtual "tour" indoors (groups of 8 or less). Upon request, we can offer theme tours such as churches, architecture, or Civil War, or even photo shoots.

$15.00

4.7/5

1 h

1-Hour Private Party Assateague Island Pony Cruise in Ocean City

Take a ride on our beautiful Skiff Boat with the family and friends! Our world-class captain will take you wherever you want to enjoy the breathtaking evening views of Assateague, Ocean City, and more! "BYOB" and enjoy the evening, or sail down south of the inlet to Assateague, where sightings of wild horses abound. We can accommodate up to five passengers. Have fun! YOU MUST ARRIVE 25 MINUTES EARLY TO YOUR RESERVATION! THE BOAT LEAVES EXACTLY AT THE TIME OF THE TRIP AND DOES NOT WAIT FOR ANYONE WHO IS LATE, SO PLAN ACCORDINGLY!

$199.99

4.3/5

2 h

Harpers Ferry Audio Tour History, Ruins and River Views

Winding through trails, town, and time, this self-guided audio tour explores the powerful stories and landscapes of Harpers Ferry. Over the course of 3 miles, you’ll journey from quiet riverbanks to dramatic ridgelines, past weathered ruins and historic landmarks that shaped the course of American history. This is no ordinary walk—it’s a deep dive into a place where freedom was fought for, ideas were tested, and the nation’s future often hung in the balance. From John Brown’s bold raid to the legacy of Storer College, each stop brings to life a new chapter of ambition, conflict, and change. With GPS-triggered audio guiding your way, you can explore at your own pace—pausing for a scenic view or reflecting at a historic site. Whether you’re a history lover, a curious traveler, or just here for the beauty, this tour offers a moving and memorable way to experience Harpers Ferry.

$9.99

4.5/5

1 h

Baltimore Bewitched: Raven's Revenge, Bones & Ballads Ghost Tour

Embark on a spine-chilling journey through Baltimore's shadowy streets with our captivating walking ghost tour, where history and hauntings converge. Guided by an experienced local, you’ll explore some of the city’s most haunted and historic sites. From the chilling whispers of bygone days to the eerie ambiance of the night, every step immerses you deeper into Baltimore’s haunted lore. Over the course of this mile-long tour, visit legendary spots such as Max’s Taphouse, where the spirits of the past may still be raising a glass, and Bertha’s, known for its ghostly patrons. You’ll also explore the somber Fell Family Cemetery, steeped in sorrow and spectral sightings, and The Horse You Came in On Saloon, a historic tavern famous for its ghostly encounters. Even as we admire privately owned buildings from the outside, you’ll be immersed in haunted ground throughout the evening, surrounded by the echoes of Baltimore's dark past.

$26.00

4/5

2 h 30 mins

Murder Mystery Detective Experience in Hagerstown MD

Step into the shoes of a newly-minted detective, tasked by Commander Mahoney to solve a gripping case... on the streets of Hagerstown. Throughout this crime-solving audio adventure, visit each of the 10 mapped locations. You'll have the option to explore the downtown area using the Walking Map or follow a Driving Map on the city's outskirts. Refer to ‘Meeting Point’ for the starting locations. See images for route. Park or stop at each location, listen to the audio story, and put your detective skills to the test by gathering clues and piecing together the evidence. Finally, make your deductions and issue an arrest warrant. Your overall detective skills will be evaluated, culminating in a Case Performance Score to measure your sleuthing prowess. This game is suitable for solo detectives, dynamic duos, or groups of mystery enthusiasts, offering an immersive audio tale filled with intrigue.

$14.99

4.7/5

1 h

1-Hour Sea Rocket Sunset & OC Harbor Cruise in Ocean City, MD

Come relax and unwind with us aboard the famous “Sea Rocket” while we check out the iconic fishing boats and restaurants/ bars in the Ocean City harbor, surrounding mansions, and search for dolphins in the Atlantic Ocean or Assawoman Bay all while watching the sun set over the Ocean City skyline! The Sea Rocket now also has a full liquor license onboard for the 2025 season as well as non-alcoholic drinks. Drink packages are available for purchase during checkout! YOU MUST ARRIVE 25 MINUTES EARLY TO YOUR RESERVATION! THE BOAT LEAVES EXACTLY AT THE TIME OF THE TRIP AND DOES NOT WAIT FOR ANYONE WHO IS LATE, SO PLAN ACCORDINGLY!

$39.99

4.6/5

2 h

Baltimore Boos & Booze Haunted Pub Crawl

Join us for a Baltimore Haunted Pub Crawl and add some fun to your work week or vacation! Explore several local watering holes and haunted hotspots on this unique, exciting tour. This tour will take you to several pubs in Baltimore, which may be a combination of craft producers and local bars. There will be a variety of haunted stops in between these already notorious bars and pubs, so by the end of the tour, you'll be a ghost expert! Grab your first drink at Max's Taphouse as your guide begins your haunting and historic journey through downtown Baltimore. From there, you'll have the chance to enjoy drinks at 3 other popular pubs and explore some other haunted locations in between. Hear stories of the Fell Family Cemetery while standing on haunted ground. Step back in time and hear the dark history behind the Waterfront Hotel. Enjoy your last drink at the Cat's Eye Pub before going home to tell your friends all about what you learned, saw, drank, and maybe even felt!

$29.00

4.8/5

1 h

Glow in the Dark Splatter Paint Experience

Immerse yourself in a glow-in-the-dark art adventure, where this brings an unforgettable community experience. Unleash creativity in a judgment-free zone, bonding over paint and tunes with loved ones. Dive into unique moments: from mastering abstract techniques to dancing as you splatter paint, every stroke is a step towards a luminous masterpiece. Your experience is customizable, ensuring it resonates with your vibe. What sets this experience apart are the key moments that make it truly unforgettable: -Personalized Music Selection: Engage in the creative process while listening to your favorite tunes, adding a personal soundtrack to your art-making journey. -Protective Gear: goggles, gloves, and hazmat suits, you'll feel like a true art scientist, ready to experiment without worrying about splatters and spills. This playful aspect adds an element of whimsy and carefreeness to the experience. -Interactive Art Techniques: Learn and apply various abstract techniques and create art

$40.00

5/5

10 mins

Downtown Baltimore Helicopter Tour

Celebrate in style with MyFlight Tours' private Baltimore downtown helicopter tour! Perfect for birthdays, anniversaries, and special occasions, this unforgettable experience offers stunning views of the city’s iconic skyline as soon as you lift off from the pier. Soar over the Inner Harbor, marvel at the towering Transamerica Tower, and glide past M&T Bank Stadium and Baltimore’s vibrant neighborhoods. Make your next celebration one to remember from the skies!

$152.50

4.5/5

2 h

The Original Haunted Pub Crawl by Annapolis Ghost Tours

The only Haunted Pub Crawls permitted inside the oldest and most haunted pubs in Historic Downtown Annapolis. Enjoy a 2-hour guided adventure on our haunted pub crawl. Drink in the history, but try not to crawl out the door! Clink glasses with a long-dead barmaid, a "working girl" who'll fall for you, a ghost whose beer has a head even though he doesn't! Join us as we walk from pub to tavern to bar and into the same watering hole, and thru the same streets and alleys as our Founding Father! Hear tales so spooky, "they'll scare ya sober!", lol! Scary? Yes...because they are real! You'll spend about 30 mins at each bar, and your guide will give you plenty of time to purchase a drink or cocktail and then tell you the haunted tales of that location and those nearby. No stories will be told until all guests have their drinks. You'll have time to order and enjoy your drink, use the restroom, and hear the haunted tales! Then on to the next pub, possibly with a stop in the church graveyard!

$31.00

4.5/5

1 h

1-Hour Ocean Parasailing Adventure In Ocean City, MD

Parasailing is a MUST DO activity when coming to Ocean City, MD! Come soar hundreds of feet above the Atlantic Ocean with Sea Rocket! What makes Sea Rocket different in Ocean City: - We fly the full 800 feet of line allowed by federal regulations — the highest legal altitude for parasailing. - Our downtown departure point means a shorter cruise to the parasailing grounds, so more of your trip is spent in the air instead of getting there - Free onsite parking a rarity for a downtown Ocean City activity - Years of Ocean City operations with thousands of flights logged and a safety-first record Please keep in mind that our crews are in the local tourism and service industry and rely heavily on gratuity from customers! Our team is here to make sure you'll have an unforgettable and safe adventure on the water! Book now to reserve your spot! Arrive 30 minutes before your reservation. Boats depart exactly on schedule and cannot wait for late arrivals, so please plan accordingly.

$94.99

Full Day Yosemite National Park Tour from Oakland

Explore and relish the enchanted day trip to Yosemite from SFO -something you don’t want to miss. Enjoy the great the great outdoors with both guided sightseeing and free time, ensuring you see the UNESCO World Heritage Site’s major attractions, like Half Dome, Yosemite Falls, and Yosemite Valley. Travel through the Central Valley farmlands, historical Gold Country, and the Sierra Nevada foothills Spend hours snapping photos of Yosemite’s stunning forests, rock formations, and waterfalls Visit Half Dome, Yosemite Falls, and El Capitan on a guided van tour. Enjoy free time to explore Yosemite’s other natural wonders by foot or bike. Take in a breathtaking panorama from the Tunnel View overlook for an expansive view of the Yosemite Valley. Small-group tour with a private and group options limited to 5 ensures a more personalized experience.

$530.00

4.5/5

The Original Fells Point Ghost Walk by Baltimore Ghost Tours

We are Baltimore’s original and only locally owned and operated haunted tour- since 2001! Our 1- 1.5 hour Original Fells Point Ghost Walk is located in Baltimore's waterfront Fells Point neighborhood and includes • Hair-straightening tales of haunting spirits from real-life events • An in-depth and unique perspective on Fell's Point history • Temporarily, all tours will be departing from the Fells Point Square near the Main Entrance of Max’s Taphouse at 733 S. Broadway, Baltimore, MD 21231.

$26.00

5/5

1 h 45 mins

Annapolis Historic Walking Tour: Harbor and Colonial Downtown

Take a pleasant walking tour through the beautiful historic center of Annapolis, including the picturesque harbor and US Naval Academy. We'll see the Georgian mansions, the iconic Maryland State House, and much more as you learn the fascinating story of the town. We'll see where the Treaty of Paris was signed (bringing to a conclusion the Revolutionary War) and where General Washington resigned as general, thus becoming the "greatest man in the world" and the "American Cincinnatus. " We'll explore the campuses of two institutes of learning that have shaped American culture. We'll walk along the city dock, harbor, and see the view to the Chesapeake Bay and wider world. I'll also share personal and family stories along the way, to add a personal dimension to the tour. I welcome all questions and special interests for our tour!

$235.00

4.9/5

4 h

Baltimore Walking Foodie Tour in Fells Point

We do 3 things: Food, facts and fun! Welcome to Fells Point, the true heart of Baltimore. Picture this: cobblestone streets lined with charming eateries, bustling markets, and hidden gems just waiting to be discovered. Join us as we guide you through Fells Point, where you’ll savor iconic dishes like mouthwatering Maryland crab cakes, fresh multi-ethnic exclusive offerings, and no fillers! Each stop is a celebration of Baltimore’s culinary heritage, and our passionate guide will share captivating stories about the area’s rich history and cultural influences. Whether you’re a seasoned traveler or new to food tours, this experience is perfect for everyone! Connect with fellow food lovers as you explore the lively atmosphere, sample delicious flavors, and soak in the stunning waterfront views. Don’t miss your chance to taste the magic of Fells Point! Book your culinary adventure today and uncover why this neighborhood is a must-visit destination for food enthusiasts!

$104.00

3.8/5

2 h

An Epic Scavenger Hunt: Baltimore Inner Harbor & Outer Sights

Let’s Roam is the top app-led adventure hunt company! Explore the most exciting landmarks and uncover hidden gems while tackling trivia questions and exciting challenges. Collaborate with your team or engage in friendly competition as you discover new facts and make unforgettable memories. Let’s Roam Adventure Hunts are perfect for any occasion—whether it's a casual outing, a lively bachelorette bash, a celebratory birthday, or a dynamic corporate team-building event! Each participant selects an interactive role, with personalized challenges to suit their skills and interests.

$12.31

4.6/5

1 h 15 mins

Baltimore Indoor Skydiving Experience with 2 Flights & Personalized Certificate

Feel the thrill of skydiving without jumping out of an airplane. It's true! Head to iFLY Baltimore, a premier indoor skydiving facility powered by a state-of-the-art vertical wind tunnel. After a training session, you'll experience free-fall conditions with the help of an instructor. No experience is necessary, and afterward, you can take home a personalized flight certificate.

$101.00

4.8/5

OC Bay Hopper - Assateague Island Cruise

How did the ponies get there? Did they swim? How many ponies live there? Can you pet the ponies? Can you feed the ponies? The answers to these questions, facts about the island, and the other amazing wildlife living on - and around - Assateague can be answered by your knowledgeable and wise captain. This is a trip you will not forget. Oh, we should mention that if you have kids and you bring them on this trip that they will love you forever!