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Chestertown

Chestertown, MD , USA

Chestertown

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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

10

What to Do in Chestertown, Maryland

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Stays

Things To Do
Provided byViator

4.6/5
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.

$112.00
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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
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4.2/5
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
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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
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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
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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
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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
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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
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4.4/5
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
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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
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4.6/5

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
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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
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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
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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
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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.

$102.00
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4.8/5
3 h 30 mins

Fells Point Food Tour in Baltimore

This 3.5 hour tour explores parts of Baltimore's best preserved historic district, Fell's Point  is a spirited waterfront community founded nearly 280 years ago.  Enjoy Fell's point amazing atmosphere and historic roots while tasting a little of what makes Fells point the place to be in Baltimore.

$78.00
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5/5
2 h

Original Fells Point Haunted Pub Tour by Baltimore Ghost Tours

Step through the doors of some of Fell’s Point’s most haunted pubs for a fascinating haunted pub crawl tour of this historic maritime neighborhood. Taverns in Fells Point have always been the rowdy stomping grounds of locals and visitors alike looking for a good time and a drink, and today it’s no different. Join the crowd and belly up to the bar like times past. Each haunted pub tour is unique with our tour guides providing their favorite haunted tales from our book, Baltimore's Harbor Haunts: True Ghost Stories, combined with their own personal ghostly experiences over the years. All of our tour guides have worked for us for at least five years, with the most seasoned guides having over 20 years of experience with us, and 20 years of ghostly tales to regale the group. The Fells Point Haunted Pub Tour is for ages 21 and older only, and is a public group tour. You will visit 3-4 haunted pubs during the tour with a tour length of 2-2.5 hours, depending on the tour guide.

$29.00
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5/5
2 h

Baltimore's Private Cultural Tour

Our Baltimore Cultural tour allow you to get a personal perspective of why Baltimore is called "Charm City".

$220.00
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5/5
1 h 30 mins

NEON Starry Night Sip and Paint Experience

Unlike a typical sip and paint, the Immersive Neon Starry Night Sip & Paint at Neon Paint Place surrounds you with moving projections, glowing stars, and vibrant music that bring Van Gogh’s masterpiece to life. Guests don’t just paint—they step into an interactive, multi-sensory environment where the art, the atmosphere, and the experience become one. With neon paints, blacklight effects, and a fully immersive starry sky, your canvas will glow long after the night is over. This BYOB event includes snacks, water, all materials, and even a take-home box for your masterpiece, making it a one-of-a-kind creative night out you won’t find at most sip and paint studios.

$40.00
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4.3/5
1 h

Ashes and Apparitions of Annapolis Ghost Tour

Embark on this Annapolis ghost tour and step back in time as you stroll through the historic district. Your guide will share chilling tales of hauntings at iconic buildings. Discover the restless spirits said to haunt Middleton Tavern, a historic site with numerous ghostly encounters. Throughout the evening, you'll traverse haunted ground, feeling the eerie presence of the spirits rumored to inhabit these locations. This mile-long trek will take you to some of the most haunted and historic sites in Annapolis, including the James Brice House, with its dark past, and the John Brice II House, where former inhabitants are said to still make their presence felt. This walking tour offers an entertaining and immersive experience into Annapolis's haunted history. Perfect for history buffs, or anyone seeking a thrilling evening, this tour promises to captivate and chill. Join us to uncover Annapolis's ghostly past and the spine-tingling stories that have been passed down through generations.

$26.00
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