Issues to Do in Chestertown MD: Japanese Shore Journey Information

Wish to step right into a residing postcard? Chestertown, Maryland, has all the pieces you need in a small coastal city: walkable historic streets, pleasant folks, distinctive eateries and indie outlets that really feel extra like treasure hunts than retail.

Historic Chestertown Maryland

Chestertown has a everlasting spot on our must-visit record.

Nestled alongside the Chester River, Chestertown, on Maryland’s Japanese Shore, could also be off the crushed path, however that’s precisely what makes it so particular. With huge character and historic colonial appeal, this distinctive small city could also be one in every of America’s coolest under-the-radar locations.

As soon as an necessary port metropolis based in 1706 and nestled alongside the banks of the Chester River, immediately you’ll be able to stroll via peaceable brick-lined streets lined with 18th-century properties, go to historic landmarks, and store your method via a city that feels prefer it was embellished for a Hallmark film set. Besides this one is actual.

Chestertown’s downtown and historic district, listed on the Nationwide Register of Historic Locations, is house to Washington Faculty, the primary school chartered in the US in 1782.

This pleasant city is filled with character. And there’s loads to do inside a couple of sq. blocks. In search of extra Maryland Japanese Shore locations? Discover close by St. Michaels, MD and Kent Narrows.

Issues to Do in Chestertown MD

Discover Historic Fountain Park

Begin your day at Chestertown’s small however lovely Fountain Park on the intersection of Excessive and Cross Streets within the coronary heart of city. A gathering place all year long, it’s additionally house to the Hebe Fountain, one in every of Chestertown’s iconic historic landmarks.

An emblem of the city’s timeless appeal, it’s one of many many public artwork installations all through the city.

Put in in 1899, manufactured from forged iron, painted turquoise, and totally practical, you’ll be able to’t miss it. Embellished fantastically with carved lions and swans, its standout characteristic is the Greek goddess of youth, Hebe, who pours “ambrosia” right into a chalice on the fountain’s prime.

Go to the Chestertown Farmers Market

Each Saturday from 8 to midday, right here you’ll discover the year-round Chestertown Farmers Market, the place you’ll be able to store for native contemporary produce, eggs, meat, dairy, flowers, baked items, and artisan crafts.

Stroll the Historic Waterfront

When you’re visiting Chestertown for the primary time, don’t miss the possibility to walk alongside its historic waterfront the place you’ll be able to get pleasure from shaded benches, river views, and a quiet place to loosen up with espresso or a picnic. It’s a well-liked birdwatching spot the place ospreys, hooded mergansers, nice blue herons, and different native birds make common appearances.

Docked on the Chestertown Marina, you can too see the Schooner Sultana, a shocking duplicate of an 18th-century British Navy vessel. It’s typically open for public sails or dockside excursions throughout particular occasions.

Take a River Cruise

For extra time on the Chester River, e-book a cruise on The River Packet. This 65-foot, Nineteen Twenties-style traditional yacht and tour boat affords weekend brunch, dinner, sundown and informal excursions April via November that go away proper from the Excessive Avenue Dock.

For extra waterfront eating experiences, try Dock and Dine Kent Narrows MD.

Attend Chestertown Festivals and Occasions

Catch a present on the Garfield Heart for the Arts on the Prince Theater housed in a fantastically restored Nineteen Twenties theater or plan your go to round one of many many yearly occasions in Chestertown just like the Chestertown Jazz Competition or the Sultana Downrigging Competition every fall which is the biggest annual gathering of tall ships in North America mixed with bluegrass music.

Throughout the Christmas season, come for ‘A Dickens of a Christmas’ competition weekend the place you’ll be able to “step again into 1840s London and expertise the vacation season as Charles Dickens imagined it.” Actions embrace complimentary carriage rides via historic downtown, a ticketed home tour, meals distributors, an artisan village and an genuine Victorian tea time. Sporting your Victorian greatest is very inspired.

Get Cozy With Pleasant Felines on the Cat Colloquium

Chestertown’s Cat Colloquium (215 Excessive St #2C, Chestertown, MD 21620) run by nonprofit Package Care Inc. is a heat, welcoming and distinctive spot for cat lovers. Right here you’ll be able to meet and snuggle up with resident cats, get pleasure from quiet time, or chat with their pleasant volunteers.

Stroll via the alley subsequent to Stam’s Luncheonette and comply with the indicators to the second ground. The area is shiny, peaceable and playful, with cozy seating, cat-friendly furnishings (together with a life-sized cat tree).

It’s a real hidden gem and a novel expertise for those who’re an animal lover like us and may’t cross up an encounter with a furry good friend. Visiting is free, however you’ll be able to try their weblog and donation choices to be taught extra and assist their native rescue efforts.

When you’re touring with 6 folks or extra, make an appointment earlier than you go. For extra tips about touring with pets, try our cat well being suggestions.

Go to Lockbrier Farm for Recent Produce and Home made Ice Cream

For a farm expertise, an eight-minute drive from downtown Chestertown, go to Lockbrier Farm to select berries, flowers and pumpkins, savor farm-churned ice cream, and replenish on contemporary, native and seasonal produce.

Since 1993, the Lockwood household—whose farming roots stretch again to the Civil Struggle—has opened the gates of Lockbrier Farms (10051 Worton Rd, Chestertown, MD 21620) to guests looking for contemporary air, vibrant blooms, and the enjoyment of choosing their very own seasonal produce.

Throughout our latest fall go to, they had been brimming with mums, pumpkins, Indian corn and gourds in each colour. Seasonally, you’ll be able to choose your personal fruits like strawberries, blueberries, raspberries, and blackberries. Wander via their flower and herb gardens, the place you’ll be able to minimize your personal to create your personal DIY bouquet.

Then store the farm stand and replenish on contemporary produce, apple cider, jams, pickled veggies, native honey, and treats like apple butter, eggs and contemporary cheese.

After exploring the farm, head over to their ice cream barn for a scoop of their unbelievable selfmade ice cream in 28+ rotating flavors like strawberry and lemon cookie. It’s made on-site with Lockbrier’s personal grown and regionally sourced substances and is among the greatest in Kent County.

Lockbrier Farm is open every day (climate allowing), Might via Thanksgiving, and there’s no admission price. Put on boots you gained’t thoughts getting soiled for those who plan to discover the fields.

The place to Store in Chestertown MD

When you’re tired of cookie-cutter vacationer traps, you’ll love Chestertown’s authentically unbiased spirit. It has 200 regionally owned outlets, galleries, eating places, bakeries, and cafes the place you’ll be able to take your time looking handmade items, uncommon books and discovering one-of-a-kind finds.

Twigs & Teacups

When you solely have time to enter one retailer in Chestertown, make it Twigs & Teacups (111 S Cross St, Chestertown, MD 21620). Everybody we requested for native suggestions stated it was their favourite retailer.

Approach greater than it seems to be from the skin, this 2-story store is stuffed with a curated assortment of whimsical and distinctive items full of persona, together with all the pieces from quirky kitchenware and nostalgic toys to regionally made items, stationery, books, puzzles, clothes and seasonal treasures. Give your self loads of time to browse, as a result of there’s a lot to see.

Pricing is inexpensive, and the pleasant employees, which incorporates their resident cat Jonathan, will allow you to discover a distinctive present for any event.

Chester River Wine & Cheese Co.

A number of doorways down, foodies and wine lovers should pop into Chester River Wine & Cheese Co. (117 S Cross St, Chestertown, MD 21620) This cozy connoisseur store and native favourite affords a curated number of wines from all over the world, and cut-to-order cheeses, charcuterie, olives, pickles, jam, snacks and specialty objects. Construct a picnic to take to the riverfront or collect snacks for winding down later.

The employees listed below are completely happy to supply pairings or samples, and the store typically hosts tastings and seasonal occasions. Whether or not you need a new wine to strive otherwise you’re a fromage fanatic, this store is a scrumptious detour.

The Bookplate

Guide lovers ought to head throughout the road, the place they’ll get misplaced within the cabinets at The Bookplate (112 S Cross St, Chestertown, MD 21620).

This unbiased used bookstore, which additionally sells classic prints and pottery, has an infinite choice with all kinds of genres and exhausting to seek out titles. The choice right here is really one in every of a form, and the books are effectively organized. If there’s one thing you need however don’t see, ask the employees, they usually could have it hidden within the stacks or can particular order it.

The place to Eat in Chestertown MD

With a lot to do right here, there’s little doubt you’ll get hungry. Once you wish to eat, Chestertown has a scrumptious mixture of choices, from Chesapeake seafood, farm-to-table fare, worldwide flavors, informal eats and comfortable consolation meals.

Stam’s Luncheonette

For an informal chew, Stam’s Luncheonette (215 Excessive Avenue, Chestertown, MD 21620) is a retro-style lunch counter, soda fountain and ice cream store in a restored area that was initially Chester Pharmacy, opened by an area named John Stam about 175 years in the past.

The mantra right here is nostalgic appeal serving up informal and traditional American lunch staples like Pizza Grilled Cheese, Dill Rooster Salad sandwiches and tomato soup. Our favourite is their well-known signature juicy Butter Burger served with cheddar cheese, caramelized onions, and on a buttery toasted brioche bun. It’s oh so buttery and value each darn calorie.

A neighborhood favourite is their in-house made ice cream and sundaes made with inventive rotating seasonal flavors like Oatmilk Chai and Honeycomb + Graham Cracker. They even have pints of ice cream to go. It’s a must-stop for those who’re craving cozy consolation meals with flavors that by no means exit of favor.

The Kitchen on the Imperial

After 25 years within the tech world, Chef Steve Quigg traded IT consulting for culinary creativity, and is the guts behind The Kitchen on the Imperial (208 Excessive Avenue, Chestertown, MD 21620). It’s one in every of Chestertown’s most beloved informal upscale eating spots, the place each dish seems like a celebration of the Japanese Shore.

Winner of Finest Chef on the Japanese Shore three years in a row, Chef Steve crafts his farm-to-table menu impressed by what’s harvested contemporary from each the native farms and waterways. The menu modifications right here typically, and all the pieces from the dinner rolls and hand-cut fries and desserts is made in-house.

A must-try right here is the Braised Lamb Shank and the signature crab desserts with completely no filler, full of contemporary lump crabmeat, completely seasoned and paired with native produce and house-made sauces for an elevated twist. They’ve gained a number of awards for ‘Finest Crab Cake’, together with honors from What’s Up? Journal and Chesapeake Bay Journal. Pair it with their Rosemary Grapefruit Margarita or a glass of wine from their in depth curated worldwide wine record.

Open for lunch, dinner and brunch on Sundays, The Kitchen on the Imperial is closed Tuesdays.

Retriever Bar

The 21 and over Retriever Bar (337 1/2 Excessive Avenue, Chestertown, MD 21620) blends Chesapeake taste with a contemporary lounge really feel and craft cocktails. Cozy up within the lounge, seize a seat on the bar, which boasts one of the vital in depth spirit alternatives on the town, together with uncommon bourbons and whiskeys.

It’s additionally Chestertown’s go-to spot for uncooked, regionally sourced Chesapeake Bay oysters, small plates like Ceviche, Heat Goat Cheese and Pickled Beets and mains like Shrimp and Grits and Lamb Birria Tacos. Whether or not you’re sipping one thing daring or nibbling on a cheese board, all the pieces is thoughtfully crafted right here.

We love the Home Burger – a juicy double smash burger with regionally raised, grass-fed St. Brigid’s beef, American cheese, pickles, shredded lettuce slathered with bistro sauce served on a toasted brioche roll served with fries on the aspect.

For dessert, strive their scrumptious Apple Strudel with a scoop of creamy vanilla ice cream from Stam’s Luncheonette.

El Rancho Mexican Delicacies

For genuine Mexican flavors, El Rancho Mexican Delicacies (851 Washington Ave, Chestertown, MD 21620) is a couple of minutes outdoors downtown. Opening early (6:30 AM most days) it’s one of many few locations on the town the place you’ll be able to seize a full sizzling breakfast. The genuine Mexican menu affords all the pieces from omelets and pancakes to quesadillas, burritos, fajitas, and bowls and platters.

We love the tender steak and flavorful Al Pastor Mexican Avenue Tacos right here, that are served in heat, hand-pressed tortillas. We additionally ordered the rooster enchiladas, ½ crimson and ½ inexperienced, served with black beans. They had been scrumptious, satisfying and actually packed some warmth.

El Rancho is informal, inexpensive, and excellent for vacationers craving daring flavors in a laid-back setting. Our server, Jordan, was tremendous pleasant, and we’re excited to strive the spicy watermelon margarita subsequent go to. El Rancho is open 7 days per week for breakfast, lunch and dinner.

Trendy Stone Age Kitchen

Trendy Stone Age Kitchen (236 Cannon St, Chestertown, MD 21620) based by meals anthropologist and former Washington Faculty professor Dr. Invoice Schindler and writer of “Eat Like a Human: Nourishing Meals and Historical Methods of Cooking to Revolutionize Your Well being,” this bakery, cafe and espresso bar open for breakfast and lunch is a one-of-a-kind edible vacation spot.

Right here you should purchase sourdough breads, bagels, croissants, pastries and scratch-made meals for breakfast and lunch ready in response to ancestral meals traditions made with substances like natural flour and lard and cooking strategies like fermentation that create essentially the most nutrient-dense meals.

Our favourite is their scrumptious hand-rolled sourdough pretzels, which promote out quick. You can even seize refrigerated ready meals to go like fermented veggies, yogurt, cheeses and house-made liverwurst.

Bakery seating is accessible inside, but it surely fills up shortly. When it’s heat, head to their fairly courtyard outdoors. When you’re , test their calendar of lessons to be taught historical meals prep expertise like sourdough baking and fermentation.

The place to Keep in Chestertown MD

Brampton 1860

Keep longer and get up at an expensive historic Nineteenth-century boutique inn on a lush non-public 35-acre property, 1 mile from downtown Chestertown at Brampton 1860.

A TripAdvisor Traveler’s Alternative Winner, featured on The Viewpoint with Dennis Quaid listed on the Choose Registry, Brampton 1860‘s (25227 Chestertown Highway Chestertown, MD 21620) completely restored historic structure, tranquil environment, genuine hospitality and a focus to element have earned it prime rankings and a loyal following.

Get up in one of many seven thoughtfully appointed rooms and suites in the principle home or six non-public cottages scattered all through the property. Every has luxurious facilities like spa tubs, fireplaces, luxurious Comphy™ linens, sensible TVs and free Wi-Fi.

Every morning, get pleasure from a freshly ready multi-course connoisseur à la carte breakfast of their sunlit eating room with menu choices like Lemon Croissant French Toast and Apple Pancakes that change every day. Have it served on their sprawling porch, deck or breakfast room. Seasonal substances, selfmade pastries, and heat hospitality are at all times included.

All through the day, assist your self to a number of baked items after which return within the afternoon for his or her Afternoon Tea for scrumptious small plates, dessert, complimentary wine, espresso and tea. After breakfast, go to their flock of chickens after which stroll via Brampton’s formal gardens with fruit timber, trails and wild meadows that entice birds, butterflies, and small wildlife.

At night time, curl up with a e-book by the fireside, do a puzzle within the library or get pleasure from a glass of wine of their bar and lounge. We love enjoyable by the outside firepit the place we are able to see tons of stars. Don’t be shocked if their cat Squeaky comes by to maintain you firm.

With customized service, Brampton 1860 affords a novel expertise that feels each timeless and welcoming. And also you’ll have the very best of each worlds: lodging at a peaceable, luxurious, historic countryside property and the comfort of Chestertown’s indie outlets, galleries, and eating places simply 5 minutes away. Brampton is adults-only and pet-friendly. EV charging stations can be found. For the very best charges, e-book direct.

💡 Learn our full Brampton 1860 Evaluation and uncover Fall Enjoyable at Brampton 1860 for seasonal actions.

Attending to Chestertown, MD

On Maryland’s Japanese Shore in Kent County, Chestertown is:

• 1 hour from Wilmington, DE
• 1.5 hours from Baltimore
• 1.5 hours from Washington, D.C.
• 1.5 hours from Philadelphia

Driving: When you’re driving, you’ll be able to attain Chestertown by way of Route 213 or Route 301, whether or not you’re coming from the north or south.
Flying: The closest main airport is Baltimore/Washington Worldwide Thurgood Marshall Airport (BWI), about 70 miles away. From BWI, you’ll be able to hire a automobile or take a shuttle service to Chestertown.
Boating: Dock on the Chestertown Marina. Verify slip charges right here and name 410-778-3616 to e-book your transient slip.
Parking: As soon as in Chestertown, parking is free and handy. Choices embrace on-street parking on Excessive Avenue, Cross Avenue, and Queen Avenue, in addition to a number of free municipal tons with cut-off dates on Spring Avenue, Cannon Avenue, and Calvert Avenue.
Chestertown makes the right addition to any Maryland Japanese Shore itinerary. Think about it as a part of your day journeys from Washington DC or discover extra with the very best day journeys from Philadelphia for nature lovers.

Closing Ideas

Chestertown, Maryland, is a historic Japanese Shore city recognized for its brick-lined streets, colonial structure, and scenic riverfront.

Based within the 1700s, it affords an enthralling escape with over 200 unbiased outlets, galleries, and cafes, with quite a lot of issues to do and occasions.

It makes the right getaway or day journey if you wish to uncover a novel vacation spot with tons of appeal and with out the crowds.

For a peaceable and splendid retreat a couple of minutes from downtown Chestertown, keep at Brampton 1860.

Chestertown is compact however filled with issues to do!

Whether or not you’re planning a romantic weekend, a solo escape, or a family-friendly journey, Chestertown affords one thing for everybody:

• Historical past lovers can discover colonial structure and heritage websites
• Foodies can get pleasure from farm-to-table eating and selfmade ice cream
• Browse indie boutiques for distinctive finds
• Discover the historic waterfront or take a river cruise
• Choose your personal berries at Lockbriar Farms, then cool off with selfmade ice cream
• Assist native and store Chestertown Farmers’ Market (Saturdays, March–December) for contemporary produce, flowers, and handmade items

For extra charming Japanese Shore locations, discover Onancock, Virginia, Cape Charles, Virginia, The Oaks Waterfront Resort, and Chincoteague.