Wish to step right into a dwelling postcard? Chestertown, Maryland, has all the pieces you need in a small coastal city: walkable historic streets, pleasant individuals, distinctive eateries and indie retailers that really feel extra like treasure hunts than retail.
Historic Chestertown Maryland
Peaceable waterfront views alongside the Chester River in Chestertown, MD. with maritime appeal on full show | Photograph: Higher DwellingChestertown 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 overwhelmed path, however that’s precisely what makes it so particular. With massive character and historic colonial appeal, this distinctive small city could also be considered one of America’s coolest under-the-radar locations.
As soon as an essential port metropolis based in 1706 and nestled alongside the banks of the Chester River, right this moment you possibly can stroll by way of peaceable brick-lined streets lined with 18th-century properties, go to historic landmarks, and store your approach by way of a city that feels prefer it was adorned 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 residence to Washington Faculty, the primary school chartered in the USA in 1782.
This pleasant city is stuffed with character. And there’s lots to do inside a number of sq. blocks. Searching for extra Maryland Japanese Shore locations? Discover close by St. Michaels, MD and Kent Narrows.
Issues to Do in Chestertown MD
The long-lasting Hebe fountain in downtown Chestertown – an ideal spot to relaxation whereas exploring the historic district | Photograph: Higher DwellingDiscover Historic Fountain Park
Begin your day at Chestertown’s small however stunning 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 residence to the Hebe Fountain, considered one 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 absolutely useful, you possibly can’t miss it. Embellished superbly 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 high.
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 possibly can store for native recent produce, eggs, meat, dairy, flowers, baked items, and artisan crafts.
Stroll the Historic Waterfront
Stroll Chestertown’s peaceable waterfront boardwalk alongside the Chester River | Photograph: Higher DwellingIn the event you’re visiting Chestertown for the primary time, don’t miss the prospect to walk alongside its historic waterfront the place you possibly can get pleasure from shaded benches, river views, and a quiet place to chill out 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 may as well see the Schooner Sultana, a shocking reproduction 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, guide a cruise on The River Packet. This 65-foot, Nineteen Twenties-style basic yacht and tour boat provides weekend brunch, dinner, sundown and informal excursions April by way of November that depart proper from the Excessive Road Dock.
For extra waterfront eating experiences, try Dock and Dine Kent Narrows MD.
Attend Chestertown Festivals and Occasions
Catch a present on the Garfield Middle for the Arts on the Prince Theater housed in a superbly 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.
In the course of the Christmas season, come for ‘A Dickens of a Christmas’ pageant weekend the place you possibly can “step again into 1840s London and expertise the vacation season as Charles Dickens imagined it.” Actions embody complimentary carriage rides by way of historic downtown, a ticketed home tour, meals distributors, an artisan village and an genuine Victorian tea time. Sporting your Victorian greatest is extremely inspired.
Get Cozy With Pleasant Felines on the Cat Colloquium
Meet the resident cats within the Cat Colloquium’s cozy second-floor lounge | Photograph: Higher DwellingChestertown’s Cat Colloquium (215 Excessive St #2C, Chestertown, MD 21620) run by nonprofit Equipment Care Inc. is a heat, welcoming and distinctive spot for cat lovers. Right here you possibly can meet and snuggle up with resident cats, get pleasure from quiet time, or chat with their pleasant volunteers.
Stroll by way of the alley subsequent to Stam’s Luncheonette and comply with the indicators to the second flooring. The area is shiny, peaceable and playful, with cozy seating, and cat-friendly furnishings (together with a life-sized cat tree).
It’s a real hidden gem and a singular expertise in the event you’re an animal lover like us and might’t move up an encounter with a furry pal. Visiting is free, however you possibly can try their weblog and donation choices to be taught extra and help them.
In the event you’re touring with 6 individuals or extra, make an appointment earlier than you go.
Go to Lockbrier Farm for Recent Produce and Do-it-yourself Ice Cream
Lockbriar Farms bursts with fall colours and recent seasonal produce | Photograph: Higher DwellingFor 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 recent, native and seasonal produce.
Since 1993, the Lockwood household—whose farming roots stretch again to the Civil Warfare—has opened the gates of Lockbrier Farms (10051 Worton Rd, Chestertown, MD 21620) to guests in search of recent air, vibrant blooms, and the enjoyment of choosing their very own seasonal produce.
Throughout our latest fall go to, they have been brimming with mums, pumpkins, Indian corn and gourds in each shade. Seasonally, you possibly can choose your individual fruits like strawberries, blueberries, raspberries, and blackberries. Wander by way of their flower and herb gardens, the place you possibly can lower your individual to create your individual DIY bouquet.
Then store the farm stand and replenish on recent produce, apple cider, jams, pickled veggies, native honey, and treats like apple butter, eggs and recent cheese.
After exploring the farm, head over to their ice cream barn for a scoop of their unimaginable selfmade ice cream in 28+ rotating flavors like strawberry and lemon cookie. It’s made on-site with Lockbrier’s personal grown and domestically sourced elements and is a number of the greatest in Kent County.
Lockbrier Farm is open each day (climate allowing), Could by way of Thanksgiving, and there’s no admission price. Put on boots you gained’t thoughts getting soiled in the event you plan to discover the fields.
The place to Store in Chestertown MD
Downtown Chestertown’s brick-lined streets come alive with fall appeal | Photograph: Higher DwellingIn the event you’re tired of cookie-cutter vacationer traps, you’ll love Chestertown’s authentically impartial spirit. It has 200 domestically owned retailers, galleries, eating places, bakeries, and cafes the place you possibly can take your time shopping handmade items, uncommon books and discovering one-of-a-kind finds.
Twigs & Teacups
Twigs & Teacups overflows with whimsical items and distinctive residence items | Photograph: Higher DwellingIn the event 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 mentioned it was their favourite retailer.
Means 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 character, together with all the pieces from quirky kitchenware and nostalgic toys to domestically 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 reasonably priced, and the pleasant workers, which incorporates their resident cat Jonathan, will aid you discover a distinctive reward for any event.
Chester River Wine & Cheese Co.
Sampling the unimaginable choice of infused olive oils and artisan meals at Chester River Wine & Cheese Co.A couple of doorways down, foodies and wine lovers should pop into Chester River Wine & Cheese Co. (117 S Cross St, Chestertown, MD 21620) This cozy gourmand store and native favourite provides a curated choice of wines from world wide, 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 workers listed here are pleased 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
The Bookplate’s charming youngsters’s part options whimsical finds and uncommon titles | Photograph: Higher DwellingE-book lovers ought to head throughout the road, the place they will get misplaced within the cabinets at The Bookplate (112 S Cross St, Chestertown, MD 21620).
This impartial used bookstore, which additionally sells classic prints and pottery, has an unlimited choice with all kinds of genres and exhausting to seek out titles. The choice right here is really considered one of a sort, and the books are nicely organized. If there’s one thing you need however don’t see, ask the workers, 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 question you’ll get hungry. Once you need to eat, Chestertown has a scrumptious mixture of choices, from Chesapeake seafood, farm-to-table fare, worldwide flavors, informal eats and comfy consolation meals.
Stam’s Luncheonette
Stam’s Luncheonette serves nostalgic consolation meals in a restored historic soda fountain | Photograph: Higher DwellingFor an off-the-cuff chunk, Stam’s Luncheonette (215 Excessive Road, 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 basic American lunch staples like Pizza Grilled Cheese, Dill Hen 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 price each darn calorie.
A neighborhood favourite is their in-house made ice cream and sundaes made with artistic rotating seasonal flavors like Oatmilk Chai and Honeycomb + Graham Cracker. They even have pints of ice cream to go. It’s a must-stop in the event you’re craving cozy consolation meals with flavors that by no means exit of favor.
The Kitchen on the Imperial
The award profitable crab cake at The Kitchen at Imperial – a must-try when visiting Maryland’s Japanese Shore. | Photograph: Higher DwellingAfter 25 years within the tech world, Chef Steve Quigg traded IT consulting for culinary creativity, and is the center behind The Kitchen on the Imperial (208 Excessive Road, Chestertown, MD 21620). It’s considered one of Chestertown’s most beloved informal upscale eating spots, the place each dish appears 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 recent from each the native farms and waterways. The menu adjustments 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 muffins with completely no filler, full of recent 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 intensive curated worldwide wine record.
Open for lunch, dinner and brunch on Sundays, The Kitchen on the Imperial is closed Tuesdays.
Retriever Bar
The Retriever Bar’s Home Burger options domestically raised grass-fed beef | Photograph: Higher DwellingThe 21 and over Retriever Bar (337 1/2 Excessive Road, 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 some of the intensive spirit alternatives on the town, together with uncommon bourbons and whiskeys.
It’s additionally Chestertown’s go-to spot for uncooked, domestically 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 domestically 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 facet.
For dessert, strive their scrumptious Apple Strudel with a scoop of creamy vanilla ice cream from Stam’s Luncheonette.
El Rancho Mexican Delicacies
El Rancho serves genuine Mexican road tacos with hand-pressed tortillas | Photograph: Higher DwellingFor genuine Mexican flavors, El Rancho Mexican Delicacies (851 Washington Ave, Chestertown, MD 21620) is a couple of minutes exterior downtown. Opening early (6:30 AM most days) it’s one of many few locations on the town the place you possibly can seize a full sizzling breakfast. The genuine Mexican menu provides 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 Road Tacos right here, that are served in heat, hand-pressed tortillas. We additionally ordered the hen enchiladas, ½ purple and ½ inexperienced, served with black beans. They have been scrumptious, satisfying and actually packed some warmth.
See additionally
El Rancho is informal, reasonably priced, and ideal 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 every week for breakfast, lunch and dinner.
Trendy Stone Age Kitchen
Recent artisan bread cooling at Trendy Stoneage Kitchen in downtown Chestertown.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 Historic 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 accordance with ancestral meals traditions made with elements 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 too can seize refrigerated ready meals to go like fermented veggies, yogurt, cheeses and house-made liverwurst.
Bakery seating is out there inside, nevertheless it fills up shortly. When it’s heat, head to their fairly courtyard exterior. In the event you’re , test their calendar of courses to be taught historic meals prep abilities like sourdough baking and fermentation.
The place to Keep in Chestertown MD
Brampton 1860’s beautiful Nineteenth-century structure glows towards a starlit Japanese Shore sky | Photograph: Higher DwellingBrampton 1860
Keep longer and get up at an expensive historic Nineteenth-century boutique inn on a lush personal 35-acre property, 1 mile from downtown Chestertown at Brampton 1860.
A TripAdvisor Traveler’s Selection Winner, featured on The Viewpoint with Dennis Quaid listed on the Choose Registry, Brampton 1860’s (25227 Chestertown Street Chestertown, MD 21620) completely restored historic structure, tranquil ambiance, genuine hospitality and a focus to element have earned it high scores and a loyal following.
Inside Marley’s Cottage at Brampton 1860 | Photograph: Higher DwellingGet up in one of many seven thoughtfully appointed rooms and suites in the principle home or six personal cottages scattered all through the property. Every has luxurious facilities like spa tubs, fireplaces, luxurious Comphy™ linens, good TVs and free Wi-Fi.
Every morning, get pleasure from a freshly ready multi-course gourmand à la carte breakfast of their sunlit eating room with menu choices like Lemon Croissant French Toast and Apple Pancakes that change each day. Have it served on their sprawling porch, deck or breakfast room. Seasonal elements, selfmade pastries, and heat hospitality are at all times included.
Brampton 1860’s gourmand à la carte breakfast options each day specials like fluffy pancakes | Photograph: Higher DwellingAll through the day, assist your self to a choice 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 by way of Brampton’s formal gardens with fruit timber, trails and wild meadows that appeal to birds, butterflies, and small wildlife.
At evening, curl up with a guide by the hearth, do a puzzle within the library or get pleasure from a glass of wine of their bar and lounge. We love stress-free by the outside firepit the place we will see tons of stars. Don’t be stunned if their cat Squeaky comes by to maintain you firm.
Curl up with a guide in Brampton 1860’s inviting library by the hearth | Photograph: Higher DwellingWith customized service, Brampton 1860 provides a singular expertise that feels each timeless and welcoming. And also you’ll have one of the best of each worlds: lodging at a peaceable, luxurious, historic countryside property and the comfort of Chestertown’s indie retailers, galleries, and eating places simply 5 minutes away. Brampton is adults-only and pet-friendly. EV charging stations can be found. For one of the best charges, guide direct.
💡 Learn our full Brampton 1860 Evaluate 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: In the event you’re driving, you possibly can 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 possibly can lease a automotive or take a shuttle service to Chestertown.
Boating: Dock on the Chestertown Marina. Test slip charges right here and name 410-778-3616 to guide your transient slip.
Parking: As soon as in Chestertown, parking is free and handy. Choices embody on-street parking on Excessive Road, Cross Road, and Queen Road, in addition to a number of free municipal tons with closing dates on Spring Road, Cannon Road, and Calvert Road.
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 one of the 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 provides an enthralling escape with over 200 impartial retailers, galleries, and cafes, with a wide range of issues to do and occasions.
It makes the right getaway or day journey if you wish to uncover a singular vacation spot with tons of appeal and with out the crowds.
For a peaceable and opulent retreat a couple of minutes from downtown Chestertown, keep at Brampton 1860.
Chestertown is compact however stuffed with issues to do!
Whether or not you’re planning a romantic weekend, a solo escape, or a family-friendly journey, Chestertown provides 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 individual berries at Lockbriar Farms, then cool off with selfmade ice cream
- Help native and store Chestertown Farmers’ Market (Saturdays, March–December) for recent produce, flowers, and handmade items
For extra charming Japanese Shore locations, discover Onancock, Virginia, Cape Charles, Virginia, The Oaks Waterfront Resort, and Chincoteague.
Higher Dwelling makes use of affiliate hyperlinks. In the event you make a purchase order by way of them, we could obtain a small fee (for which we’re deeply grateful) without charge to you.
