Blake Walsh

20 Best Things to Do in Chestertown, MD

  • Published 2022/11/30

Chestertown is one of the oldest counties in Maryland, having been established as early as 1706 and characterized by brick sidewalks and antique shops lining the roads.

This historic colonial town is rich with maritime heritage and packed with tourist hotspots and destinations for you to visit!

This town is also complete with an arts district and center where you can find a lot of art galleries where local artworks and culture thrive.

With its amazing downtown area and welcoming and relaxing atmosphere, this town beckons guests to drop by and see all the sights, activities, and attractions they have to offer!

Explore this historic town in Kent County with this list of attractions to visit and events to attend!

Drop by the Fountain Park at Chestertown

A kid at Fountain Park

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One of Chestertown’s most well-known parks for hosting farmer’s markets and other community and local events, Fountain Park is a hotspot location for visitors and tourists!

Characterized by a recently refurbished fountain at the park’s center, this park is the perfect place to wind back and relax after a long day of touring the city.

You may take some pictures of Hebe, the goddess of youth that is carved onto the fountain, along with the ornate swans and lion heads that distinguish this multitiered fountain from the rest.

The fountain at Fountain Park

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Fountain Park is frequently used as the events space for the Music in the Park concert series, the venue for their Farmer’s Market and car shows, in downtown Chestertown!

Whether it’s a relaxing day you’re after or an adventurous one, Fountain in the Park has it for you!

Do Some Recreational Activities at Wilmer Park

This waterfront park in Chestertown gives guests a variety of outdoor recreational activities to do!

Only a short drive away from the town center, this expansive park features walking trails with a lovely view of Chester River.

Various pavilions are also scattered throughout the park, available for your use and enjoyment.

You may even have a picnic with your family on the grass if you bring a blanket or avail of their picnic tables and benches.

This park is also home to several species of birds, so keep an eye out for them or make the most out of your trip by going out into the water on a kayak or canoe!

Bring the entire family and even your pets for some great quality time at Wilmer Park!

Attend the Music in the Park Concert Series

Chestertown is known for its Music in the Park, a concert series that takes place during the summer.

With a wide range of musical genres, including jazz, rock, folk, and more, you’re bound to have a great time!

To make it even better, these concerts every Saturday are free for all!

This concert takes place in Fountain Park, a well-known recreational facility that is easily accessible at the center of this town.

Music in the Park will ensure you a good time, no matter your age and who you’re with!

Wander around the MassoniArt Gallery

MassoniArt Gallery, also known as Carla Massoni Gallery, is one of the staple art galleries in Chestertown that you should definitely visit!

Operating for over 30 years, this gallery is home to a multitude of art pieces, ranging from full projects of gallery exhibits to artworks, paintings, and portraits across a variety of mediums.

They also house different types of collections that are respected by artists, artisans, and other patrons!

More than just an art gallery for artists to showcase their masterpieces, MassoniArt Gallery also helps each artist get the recognition they deserve by aiding in their collaboration with various newsletters and publications!

There truly is a handful of artworks by skilled artists that you can find inside this gallery, so be sure to check it out!

Buy a Book at The Bookplate

Exterior of The Bookplate

Bohemian Baltimore, CC BY-SA 4.0, via Wikimedia Commons

Attention and book lovers and enthusiasts!

Stacked with the latest literary finds, this bookstore in Chestertown is complete with books from all kinds of genres, from romantic fiction to memoirs and everything in between!

Avid book worms are more than welcome to spend hours looking around the tall, wide array of shelves that carry various books.

Interior of The Bookplate

Bohemian Baltimore, CC BY-SA 4.0, via Wikimedia Commons

You’re also allowed to pick a book up and skim through it, indulging yourself in a world of written stories.

They also carry limited edition books, signed editions, and other collectibles that you can add to your collection!

These carefully selected books and pieces at The Bookplate are full of much information and entertainment just for you!

Watch Different Shows at Garfield Center for the Arts at the Prince Theatre

In promoting the arts and culture of Chestertown, Garfield Center for the Arts at the Prince Theatre hosts a variety of shows that include original theatrical plays to orchestras and musicals!

With the mission to keep the art alive, this performing arts theater is open to all artists, whether it’s playwrights, musicians, actors, and more.

You can catch a show based on their schedule and calendar of upcoming events, so be sure to come on time!

For a small fee, not only can you watch their productions and performances, but you can also get the chance to participate in their small group events that include improv and open mic nights.

Be entertained by their shows or learn a thing or two about performing arts at Garfield Center for the Arts at the Prince Theatre!

Visit Chestertown’s Brewpub at Bad Alfred’s Distilling

Since its establishment in 2018, Bad Alfred’s Distilling has been crafting some of the tastiest, most creative spirits in this town!

Guest can select a drink from their house-made options such as beers and cocktails with various twists and ingredients you’re sure to enjoy.

Paired with tasty pizza that’s been freshly cooked in a wood-fired oven, you can even satisfy your hungry stomach here!

This brewery and pub also offers a look behind the scenes as to how their spirits are made by booking a private tour.

Or sample their best spirits in a private taste room that you can avail of!

Try and drop by this distillery to get a taste of their craft spirits at Bad Alfred’s Distilling!

Enjoy a Meal at Figg’s Ordinary

Staying true to Chestertown’s colonial history, Figg’s Ordinary brings the colonial roots to the modern-day era through their food!

Since this eatery opened in 2015, they’ve been serving the community with delicious meals and pastries that can cater to anybody despite dietary restrictions and needs, including vegan, dairy-free, and wheat options.

The founder, Ingrid Hansen, named this establishment after her pet dachshund, Figgs, and their gluten-free, healthy menu was inspired by her daughter, who developed gluten intolerance.

Made only with the highest quality of ingredients that are fresh, you can enjoy a lovely meal at Figg’s Ordinary without sacrificing your dietary restrictions!

This restaurant has also been voted Best New Business of the Year by the Kent County Chamber of Commerce due to its success and has only continued to grow over the years.

Drop by this iconic eatery at the heart of Chestertown!

Purchase a Vintage Souvenir at Bee Crafty Collectibles

Situated within this historic downtown, Bee Craft Collectibles houses a wide variety of antiques, vintage items, and collectibles that can serve as the perfect souvenir for this trip!

You can find all kinds of items, from accessories to home decor and novelty items; you can shop for them here for a great price!

This establishment is committed to serving you only the best, starting with their personalization services where guests have the option to request a specially made antique.

Whether big or small – a simple personalized keychain up to custom-made furniture – Bee Crafty Collectibles will be more than willing to do it for you.

This eclectic gift shop is definitely unique in the town of Chestertown and carries one-of-a-kind items that will not disappoint you!

Explore the Wayne Gilchrest Trail

North end of Wayne Gilchrest Trail

Eplack, CC BY-SA 4.0, via Wikimedia Commons

Stretching over 1.2 miles in length on the southern edge of Chestertown, the Wayne Gilchrest Trail, formerly known as Chestertown Rail Trail, is a walking path on an abandoned railway.

This trail became open to the public on Earth Day in 2012 and has been named for a well-known environmentalist in the community and former congressman.

Since the permanent closure of this freight service in the 1990s, this path contains flat walking surfaces and gentle curves perfect for jogging, biking, and walking.

It begins on old train stations and winds through the town’s residential community that can show you the beauty of Chestertown!

You may even explore the natural habitats, admire the industrial buildings along the way, or simply take a leisurely stroll through this abandoned railway station, where you’re sure to be amazed by the interesting sites!

Go on a Cruise with Chester River Packet Co.

Chester River Packet Company offers tourists charter cruises on the Chester River where they can admire the historic town from the water!

Guests are boarded on the River Packet, a 65-foot yacht that comfortably seats about 100 people on a tour.

Since its launch in the 1990s, River Packet has been refurbished and maintained by local craftsmen to continually serve the community of Chestertown.

This spacious yacht takes on a 1920-style design, making it the perfect vessel to sail for tour purposes or used as an event space.

River Packet also hosts special events cruises, including brunches, tea parties, and more, which you can join by purchasing a ticket ahead of time.

The scenes and sights of Chester River are something you don’t want to miss, so book a cruise with the entire family!

Wind Back and Relax at Rolphs Wharf Marina

Featuring a sandbar, marina, and a river inn, Rolphs Wharf Marina ensures a relaxing getaway located along the Chester River!

Enjoy the lovely views of the sunset while you sip on a cocktail at The Sandbar or snack on some light meals you can choose from on their menu.

Occasional live music and entertainment plays on certain nights, completing the relaxing aura while you walk around the soft sand.

Guests also can book a night or two at The River Inn, where they can choose from various rooms and suites and take advantage of its adjoining farm!

The marina itself has a boat ramp that stretches out over the water and also gives you breathtaking views of the sunset!

Rolphs Wharf Marina is the go-to destination in Chestertown if you are looking to get away from the busy streets.

Participate in Art Workshops at Chestertown RiverArts

Chestertown RiverArts is another art gallery in the cultural district of this town that allows guests to take a look around various pieces of art.

Home to various exhibits across different mediums, this art gallery showcases some of the most unique and creative pieces by local and national artists.

This establishment believes that art is a great way to destress and re-energize yourself from all the worries of the world by expressing yourself on canvas or through your medium of choice.

RiverArts welcomes all locals and tourists alike, seeking to grow their art community and watch it thrive with their programs, activities, and events.

This space also cultivates an environment for people with shared love and interest for the arts!

Found within the town center, this art gallery is easily accessible, so be sure to add this place to your itinerary!

Drop by Chestertown’s Tiki Bar at Jellyfish Joel’s

Located on Chestertown’s Fairlee Creek, Jellyfish Joel’s is best known for their seasonal drinks, live entertainment, and matching light meals!

Their menu includes a variety of seafood options, among other food items, as well as a food truck near the beach!

This tiki bar is part of the Safe Harbor Great Oak Landing and is surrounded by other amenities, giving you a wide list of things to do.

Near Jellyfish Joel’s, you can find a 9-hole golf course where you can challenge your family and friends to a friendly game.

With a lovely view of the water, a refreshing drink in your hand topped off with a cool breeze brought by Chestertown’s waterfront, it can’t get any better than this!

Learn about the Rich History of Chestertown at The Historical Society-Kent County

The Historical Society-Kent County is a museum dedicated to preserving the rich history of Chestertown; its colonial roots can be traced back to its establishment in 1706 and the entirety of Kent County!

This museum can be found inside a rebuilt building within the Bordley History Center, a historical establishment in Chestertown.

Complete with rotating and interactive exhibits, this museum has a lot of information to share with you that’s bound to pique your interest through presentations, publications, researches, and more.

These exhibits also change two or three times annually, providing guests with a change and variety where they can learn something new.

Not limiting themselves to the museum’s walls, this non-profit organization also offers tours all over town, with visits to Chestertown’s architectural landmarks built in the 18th and 19th centuries, the different African-American heritage sites, and even trips to the abandoned underground railroad tracks!

There truly is a lot to learn, see, and do at The Historical Society-Kent County, so be sure to drop by to complete your trip!

Stock on Delicious Food Supplies from Chester River Wine & Cheese

John Laucik and Jennifer Baker own and run Chester River Wine & Cheese, a popular establishment in Chestertown’s bustling Arts & Entertainment neighborhood.

They strive to provide fantastic dinners, lovely memories, and a peaceful environment for regular foodies.

Cheese, wine, freshly frozen pasta, olives, and antipasti are available at the store.

Beef, chicken, hog, lamb, and duck are the frozen meats sold in the store.

Additionally, they feature a specialty grocery store that sells pickles, vinegar, mustard, and jam.

They are the sister establishment to Welcome Home, which has outlets in Chestertown and Annapolis and sells kitchen and practical home supplies.

Explore through a Self-Guided Tour at Chesapeake Farms

On its 3,300 acres, Chesapeake Farms is dedicated to researching, testing, and presenting cutting-edge agricultural methods and nature conservation strategies that are intended to be productive, ecologically friendly, and socially appropriate.

Take a self-guided tour to Chesapeake Farms, where various stops contain information on what to explore.

The trip starts in the primary waterfowl rest site of the Farms, which is across from the main office building.

They maintain their forests to produce firewood, wildlife habitat, and aesthetic value.

Along the journey, you can witness birds, mainly wood ducks, using artificial nesting formations.

Dine in a Relaxing Atmosphere at Luisa’s Cucina Italiana

Since 2000, Luisa’s Cucina Italiana has been run by a chef and features a relaxed, rustic-modern, and welcoming setting for families.

The restaurant offers a wood-fired pizza oven, a stunning granite cocktail lounge, and true, straightforward food made with regional ingredients.

Pick from their extensive menu of pizzas; every pizza comes with mozzarella and Luisa’s sauce on top.

Additionally, they provide other toppings, including onions, bell peppers, mushrooms, bacon, pepperoni, sausage, and extra cheese.

You will undoubtedly find something delectable to share with your friends and family, whether for lunchtime, dinner, takeaway, or a beverage at the bar!

Book a Room at the Brampton Bed and Breakfast Inn

Front view of Brampton Bed and Breakfast Inn

JERRYE & ROY KLOTZ, M.D., CC BY-SA 4.0, via Wikimedia Commons

On the Eastern Shore of Maryland, the legendary Brampton Inn is situated on 35 acres of beautiful gardens, meadows, and woodland.

The modest hotel is only a short distance from Washington College, situated on the picturesque Chester River.

Brampton Bed and Breakfast Inn provides seven expansive rooms and suites in their lovely manor home and six individual cottages for a total of thirteen distinctive accommodation options.

The rooms and remote cottages provide unmatched tranquility with wood-burning fireplaces and contemporary ensuite baths.

Each has been thoughtfully outfitted with private bathrooms, high-end bedding and bath items, smart TVs, and quick wireless internet to maximize customer comfort.

The daily menu varies for their freshly made à-la-carte breakfast.

Dine and Mingle in The Kitchen at The Imperial

Cook and proprietor Steve Quigg decided to change occupations in 2010. He closed his IT consulting business, relocated to the Eastern Shore with his household, and bought a modest coffee shop.

As a product of that choice, the informal fine dining establishment The Kitchen at Rock Hall became a tremendously successful business with a massive presence of devoted patrons and multiple accolades for the food.

The Kitchen at the Imperial is a spot where new friends may discover a nice welcome, a refreshing beverage, and a contemporary American menu prepared with passion.

Depending on the supply of fresh, regional products, The Kitchen at The Imperial’s menus is subject to regular modification.

Additionally, they host weekly wine tastings beginning at 6 pm.

There are little snacks provided; however, you may always make an evening of it by staying for dinner.

Final Thoughts

This historical town is packed with many things to do and sights to see despite its reputation as a calm, relaxing destination in Maryland.

From museums to walking trails, classic eateries and antique stores, and everything in between, Chestertown has it all for you!

This rural district is the ideal place if you’re looking for a relaxing getaway where you can do everything, but also do nothing at all, and still have a great time!

The location of this town next to a body of water provides a relaxing, homey aura that is sure to give you a break from the loud hustle and bustle of the city.

With serene views and a peaceful atmosphere, Chestertown has a lot to share with you, so book a trip now!

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