Explore Chestertown, Maryland: Small Town, Big Fun

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Chestertown, Maryland, has a fascinating history. Combined with great food, drink, and lodging, Chestertown is a must-see when you visit Maryland. Read on for why you need to explore Chestertown, MD.
Chestertown, MD, is one of my favorite towns on the Eastern Shore. My wife and I have been visiting Chestertown for over ten years. While other towns like Rock Hall, Easton, and St Michaels are fun to explore, Chestertown has our favorite bakery , farmers market, and fascinating history. I’ll take you for a tour of the town to show why you should include Chestertown on your next trip to Maryland.
A Deep History of Chestertown, Maryland
In 1706, Chestertown was founded on land donated by Simon Wilmer, who owned ample property in Kent County. Wilmer’s estate included Stepney Manor, built around 1690. What I love about Chestertown is the well-preserved homes, some dating back to the 1730s. On a recent trip, I stopped at the visitor’s center and picked up a brochure for the historic walking tour.
There are 25 stops on the walking tour, and the unseasonably warm April day was perfect for the self-guided tour. Some of the tour’s highlights were Widehall, stop #1, built in 1770 by Thomas Smythe, a wealthy businessman. The home sits on the corner of Water Street and High Street, overlooking the Chester River. Widehall is an excellent example of Georgian architecture. I suspect some great parties were held inside and out in the manicured backyard.
Widehall is on a large corner lot overlooking the Chester River. Photo by Kurt Jacobson
Old School Architecture
Just up the street is another home once owned by Mr. Smythe called River House. This mansion is an example of Federal-style architecture and is in excellent condition. Homes on Water Street sell for around $1,100,000 and up, per a realtor I met while on the walking tour. The fourth stop on the tour is the Watkins-Bryant House, a wedding gift from Esau Watkins’ in-laws, built in 1730 and thought to be the oldest home on Water Street.
The Wickes House was built in 1767, home of the well-known family who helped shape Chestertown into one of the most important towns in early Maryland history.
A Historic Inn
After seeing the other homes on the list, I came to the White Swan Tavern, built in 1733, originally as a residence. In 1790 the home was converted into a tavern and later a general store. The tavern was restored in the 1970s as a bed and breakfast. If you stay here, you can tell your friends that you slept in a place that George Washington stopped at for refreshments during one of several visits to Chestertown.
The newly renovated dining room at the White Swan Tavern is an elegant place for breakfast. Photo by Kurt Jacobson
African American History
The Grand Army of the Republic Charles Sumner Post #25 was one of the more interesting stops on the walking tour. After the Civil War, 28 African American Civil War veterans founded post #25 in 1882. The post became a cornerstone of the African American community in and around Chestertown for many decades. Once there were over 500 Maryland G.A.R. posts, 22 of which were African American. Post #25 was nearly destroyed, but dedicated community members renovated the building now known as Sumner Hall. The Hall holds programs and exhibitions to honor African American veterans.
Uncommonly Good Eats in Chestertown, Maryland
I first came to Chestertown to investigate the rumor that Evergrain Bread Company was one of the best bakeries in Maryland. Since that first visit, I’ve been back over a dozen times to buy the everknots—a croissant dough creation baked in a round with a dollop of cream cheese, peach/ginger scones, buzz bars, and whatever else looks good that day.
A delicious lineup of baked goods awaits customers at Evergrain in Chestertown, Maryland. Photo by Kurt Jacobson
Owner Douglas Rae is a gifted bread baker who started baking while still in high school. After graduating from culinary school, he traveled the US working at excellent bakeries as an intern for three months each. Doug’s customers come from near and far to enjoy the bread, sweets, and barista-made coffee and grab a sidewalk table. Douglas will open another bakery at his recently purchased local farm and serve his tasty baked goods and pizza.
Dinner at the Imperial
Across the street from Evergrain is The Kitchen At the Imperial. Whether for lunch, dinner, or brunch, The Kitchen delivers a good time. On my recent stop, I had the polenta and mushroom appetizer with a glass of Champagne at the bar before grabbing a seat in the dining room. The dinner menu featured oysters, crab dip, crab soup, kale salad, and other delicious appetizers. For entrée choices, the braised lamb shank won me over, even though the crispy cod was a close second.
I enjoyed a glass of Champagne at the Imperial’s vintage bar. Photo by Kurt Jacobson
Fire Up the Wayback Machine
The Modern Stone Age Kitchen is a restaurant like no other. Owned and operated by Dr. Bill Shindler and his family, this place impressed me with its concept of eating like our human bodies were designed to eat. Dr. Bill used to teach Archeology and anthropology at nearby Washington College. He has tailored his menu from years of researching ancient indigenous diets and how we can mimic some of our ancestors’ foods.
Modern Stone Age Kitchen owners chat with customers on the patio. Photo by Kurt Jacobson
Fermented foods are the bulk of the items on the menu. The cooks make everything from scratch using traditional methods to ensure the food is as nourishing as possible. I like that they don’t use any industrial fats or refined sugar.
Modern Stone Age Kitchen’s sourdough creations bread has may fans. Photo by Kurt Jacobson
Modern Stone Age Kitchen features pizza night every Friday; everything on the pizza is made in-house. The baked goods are all made with sourdough starter and high-quality grains. Make sure to check out the pretzels or the croissants as I thought both were delicious.
Several locals told me the new hot restaurant is Watershed Alley, but it was closed when I was in town. I plan on trying it next time I visit Chestertown.
Where to Stay in Chestertown, Maryland
The White Swan Tavern is within walking distance of all the town’s best eateries, shops, and bars. Recent renovations have made the tavern shine. The tavern updates took place from January to mid-April, combining old-world charm with modern conveniences.
I got a sneak peek inside the White Swan Tavern shortly after renovations were completed. I was very impressed with the common areas’ decorating, cleanliness, and comfort. Innkeeper Beth Lavery showed me the oldest room at the tavern, the John Lovegrove Kitchen. The room featured the best of old and new. The bathroom was modern, clean, and functional. The bedroom included an old fireplace used for cooking during the early days. The antique kitchen included a Dutch oven, a kettle, and other implements in a 17th Century kitchen.
The White Swan Tavern guest rooms offer the best of old and new. Photo by Kurt Jacobson
Out back is a private yard and patio for relaxing away from the bustling scene on High Street. There are parking spaces reserved for guests behind the Inn.
A Second Historic Place to Stay in Chestertown, Maryland
Brampton Inn is on the outskirts of town on Route 20 towards Rock Hall. The Inn was built in 1860 and sits on 30+ acres of gardens and woods for a peaceful setting. Six delightful cottages offer privacy and comfort. Two of the cottages are pet friendly for those who want to bring Fido. The pet fee is a reasonable $35 per pet per night.
Brampton Inn is a great place to stay just minutes from the center of Chestertown, Maryland. Photo by Kurt Jacobson
I stayed one night in the Yellow Room and loved the vibe of this well-kept Inn. With 30+ acres of woods, gardens, and pathways, I enjoyed walking the property while taking in the sights and sounds of spring. The eastern redbud trees were in full bloom, and the flower gardens seemed to be waking up and preparing for summer. Breakfast was delicious. I had the stuffed French toast and a side of fresh fruit, which held me over until lunchtime.
An Eastern Red Bud Tree was in full bloom during my visit to Brampton. Photo by Kurt Jacobson
Other Must-See Highlights
For those in the know, the best place for a drink is Zelda’s, a speakeasy owned and run by Jeff McGuire. There are no signs to guide you to Zelda’s and no posted operating hours. Zelda’s is open if the green light is on above the 108 Cross St sign.
The green light at Zelda’s was on the night I stayed in Chestertown, Maryland. Photo by Kurt Jacobson
Head up the stairs and notice the artwork, quotes, photos, and other decorations. The night I visited, a small crowd kept Jeff busy, but he still found time to chat with me as I sipped my hard cider. Zelda’s is the most authentic speakeasy I’ve ever imbibed at, and I can’t wait to come back for another round.
Jeff tending bar at Zelda’s speakeasy. Photo by Kurt Jacobson
Take a Hike Near Chestertown, Maryland
Wayne Gilchrest Trail is a Rails-to-Trails pathway I walk almost every time I visit Chestertown. My wife and I often bring our dog to Chestertown and love walking this trail in one of the most dog-friendly towns on the Delmarva Peninsula. A walk towards the Chester River takes you to Wilmer Park (good for picnics) and a waterfront pavilion.
The playground and picnic areas of Phillip G. Wilmer Park in Chestertown, Maryland. Photo by Kurt Jacobson
Away from the river past the old train station, take a nice 20-minute stroll where birds sing, and locals jog, hike, or walk dogs. Take the right fork in the trail past Lynchburg Street to see one of the oldest colleges in the US. George Washington helped fund the college named after him in 1782.
My favorite farmers market on the Delmarva Peninsula is in Chestertown every Saturday year-round at Cross and High Street. On peak market days, the vendors stretch out for two blocks. I buy fresh mushrooms from King Mushrooms, chicken from Where Pigs Fly Farm, fermented veggies from Okskana’s Produce Farm, and seasonal fruit and veggies.
The Chestertown Farmers Market is held every Saturday year-round. I like it best in summer and fall. Photo by Kurt Jacobson
Shopping
Chestertown has many mom-and-pop shops, mainly on Cross Street and High Street. The Book Plate on Cross Street pulls me in for their new and used book selection and the shop kitty, which is usually hiding. The Decoy bottle shop has a good selection of whiskey, but I like the small producer wines hand-picked by the owner, most of which are under $20. Our dog Sophie likes going to Coco’s Pet Boutique in hopes of getting a new toy or dog treats.
I stopped in at Tish Fine Art Plus for a look and saw several examples of Chesapeake Bay art by over 20 artists. For food and wine, I love Chester River Wine and Cheese for olive oil, pasta, wine, cheese, and more. Speaking of wine, I’m a fan of Casa Carmen on 312 Cannon Street for their wine flights, tapas, and bottles of wine to take home.
Tish Fine Art Jewelry and Apparel is a gem in Chestertown. Photo by Kurt Jacobson
Events to Attend
In a nod to its maritime past, Downrigging Weekend celebrates Chestertown’s past as a crucial Colonial port city. This event is one of the biggest tall ship gatherings in North America. Enjoy tours, live music, regional food, and family activities during the last weekend of October.
Boston isn’t the only Colonial city to have had a tea party. The citizens of Chestertown were also fed up with the British and their high taxes and dumped a load of valuable tea in the Chester River in 1774. Celebrate this act of civil disobedience each Memorial Day, and bring your own tea just in case the town’s supply ends up in the Chester River.
Watch the Tea Party festivities in Chestertown during the Memorial Day Weekend event. Photo courtesy of Kent County Economic and Tourism
Other key events: Paint the Town, National Music Festival, Juneteenth Celebration, and more are listed at mainstreetchestertown.org . Be aware that some of these Chestertown events are so popular that many lodging establishments sell out a year in advance!
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Summary
Chestertown is one of my most-visited places on the Delmarva Peninsula. I love how pedestrian and dog-friendly the town is. With so many excellent places to eat, two great historic inns, good shopping, and proximity to Baltimore or Washington, DC, it’s easy to see why Chestertown is worth a look.
Let Wander With Wonder be your guide when planning a trip to Chestertown, another historic town , or anywhere in the Mid-Atlantic .
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Explore Chestertown, Maryland: Small Town, Big Fun
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