Wish to step right into a dwelling postcard? Chestertown, Maryland, has all the things you need in a small coastal city: walkable historic streets, pleasant individuals, distinctive eateries and indie outlets that really feel extra like treasure hunts than retail.
Historic Chestertown Maryland
Peaceable waterfront views alongside the Chester River in Chestertown, MD. with maritime attraction on full show | Photograph: Higher DwellingChestertown has a everlasting spot on our must-visit record.
Nestled alongside the Chester River, Chestertown, on Maryland’s Jap Shore, could also be off the crushed path, however that’s precisely what makes it so particular. With large character and historic colonial attraction, this distinctive small city could also be one in all 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, right now you may stroll by peaceable brick-lined streets lined with 18th-century houses, go to historic landmarks, and store your means by 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 house to Washington Faculty, the primary faculty chartered in the USA in 1782.
This pleasant city is filled with character. And there’s loads to do inside a number of sq. blocks. Searching for extra Maryland Jap 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 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 all Chestertown’s iconic historic landmarks.
An emblem of the city’s timeless attraction, it’s one of many many public artwork installations all through the city.
Put in in 1899, fabricated from forged iron, painted turquoise, and absolutely practical, you may’t miss it. Adorned superbly with carved lions and swans, its standout function 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 may store for native contemporary 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 DwellingShould you’re visiting Chestertown for the primary time, don’t miss the prospect to walk alongside its historic waterfront the place you may take pleasure in 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 can even see the Schooner Sultana, a surprising reproduction of an 18th-century British Navy vessel. It’s usually 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, Twenties-style traditional yacht and tour boat affords weekend brunch, dinner, sundown and informal excursions April by November that depart proper from the Excessive Avenue Dock.
For extra waterfront eating experiences, take a look at 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 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 may “step again into 1840s London and expertise the vacation season as Charles Dickens imagined it.” Actions embody complimentary carriage rides by historic downtown, a ticketed home tour, meals distributors, an artisan village and an genuine Victorian tea time. Carrying your Victorian finest is very 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 may meet and snuggle up with resident cats, take pleasure in quiet time, or chat with their pleasant volunteers.
Stroll by the alley subsequent to Stam’s Luncheonette and observe the indicators to the second flooring. The area is brilliant, 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 novel expertise in the event you’re an animal lover like us and may’t move up an encounter with a furry good friend. Visiting is free, however you may take a look at their weblog and donation choices to study extra and assist them.
Should you’re touring with 6 individuals or extra, make an appointment earlier than you go.
Go to Lockbrier Farm for Recent Produce and Home made Ice Cream
Lockbriar Farms bursts with fall colours and contemporary seasonal produce | Photograph: Higher DwellingFor a farm expertise, an eight-minute drive from downtown Chestertown, go to Lockbrier Farm to choose berries, flowers and pumpkins, savor farm-churned ice cream, and refill on contemporary, native and seasonal produce.
Since 1993, the Lockwood household—whose farming roots stretch again to the Civil Conflict—has opened the gates of Lockbrier Farms (10051 Worton Rd, Chestertown, MD 21620) to guests searching for contemporary air, vibrant blooms, and the enjoyment of selecting 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 may decide your individual fruits like strawberries, blueberries, raspberries, and blackberries. Wander by their flower and herb gardens, the place you may lower your individual to create your individual DIY bouquet.
Then store the farm stand and refill 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 unimaginable do-it-yourself ice cream in 28+ rotating flavors like strawberry and lemon cookie. It’s made on-site with Lockbrier’s personal grown and domestically sourced substances and is among the finest in Kent County.
Lockbrier Farm is open each day (climate allowing), Could by Thanksgiving, and there’s no admission charge. 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 attraction | Photograph: Higher DwellingShould you’re tired of cookie-cutter vacationer traps, you’ll love Chestertown’s authentically impartial spirit. It has 200 domestically owned outlets, galleries, eating places, bakeries, and cafes the place you may take your time searching handmade items, uncommon books and discovering one-of-a-kind finds.
Twigs & Teacups
Twigs & Teacups overflows with whimsical items and distinctive house items | Photograph: Higher DwellingShould 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.
Means larger than it seems from the surface, this 2-story store is stuffed with a curated assortment of whimsical and distinctive items filled with persona, together with all the things 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 inexpensive, and the pleasant workers, which incorporates their resident cat Jonathan, will assist you discover a distinctive present for any event.
Chester River Wine & Cheese Co.
Sampling the unimaginable number of infused olive oils and artisan meals at Chester River Wine & Cheese Co.Just a few 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 affords a curated number of wines from around the globe, and cut-to-order cheeses, charcuterie, olives, pickles, jam, snacks and specialty gadgets. Construct a picnic to take to the riverfront or collect snacks for winding down later.
The workers listed below are completely satisfied to supply pairings or samples, and the store usually hosts tastings and seasonal occasions. Whether or not you desire a new wine to strive otherwise you’re a fromage fanatic, this store is a scrumptious detour.
The Bookplate
The Bookplate’s charming kids’s part options whimsical finds and uncommon titles | Photograph: Higher DwellingGuide 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 infinite choice with all kinds of genres and arduous to search out titles. The choice right here is actually one in all a form, and the books are nicely organized. If there’s one thing you need however don’t see, ask the workers, and so they might 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. While you wish 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 informal chunk, 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 a neighborhood named John Stam about 175 years in the past.
The mantra right here is nostalgic attraction 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 price 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 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 successful crab cake at The Kitchen at Imperial – a must-try when visiting Maryland’s Jap 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 Avenue, Chestertown, MD 21620). It’s one in all Chestertown’s most beloved informal upscale eating spots, the place each dish looks like a celebration of the Jap Shore.
Winner of Greatest Chef on the Jap 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 adjustments right here usually, and all the things 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, filled with 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 ‘Greatest 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 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 crucial intensive spirit choices 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 things 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 outdoors downtown. Opening early (6:30 AM most days) it’s one of many few locations on the town the place you may seize a full scorching breakfast. The genuine Mexican menu affords all the things 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 pink and ½ inexperienced, served with black beans. They had been scrumptious, satisfying and actually packed some warmth.
See additionally
El Rancho is informal, inexpensive, 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 per 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 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 buy sourdough breads, bagels, croissants, pastries and scratch-made meals for breakfast and lunch ready based on 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 too seize refrigerated ready meals to go like fermented veggies, yogurt, cheeses and house-made liverwurst.
Bakery seating is obtainable inside, however it fills up rapidly. When it’s heat, head to their fairly courtyard outdoors. Should you’re , verify their calendar of courses to study historic meals prep abilities like sourdough baking and fermentation.
The place to Keep in Chestertown MD
Brampton 1860’s gorgeous Nineteenth-century structure glows in opposition to a starlit Jap Shore sky | Photograph: Higher DwellingBrampton 1860
Keep longer and get up at an opulent 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 Highway Chestertown, MD 21620) completely restored historic structure, tranquil ambiance, genuine hospitality and a spotlight to element have earned it prime rankings 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, sensible TVs and free Wi-Fi.
Every morning, take pleasure in 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 substances, do-it-yourself pastries, and heat hospitality are all the time 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 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 by Brampton’s formal gardens with fruit timber, trails and wild meadows that entice birds, butterflies, and small wildlife.
At evening, curl up with a guide by the hearth, do a puzzle within the library or take pleasure in 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 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 personalised 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, guide direct.
💡 Learn our full Brampton 1860 Evaluation and uncover Fall Enjoyable at Brampton 1860 for seasonal actions.
Attending to Chestertown, MD
On Maryland’s Jap 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: Should you’re driving, you may 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 may 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 guide your transient slip.
Parking: As soon as in Chestertown, parking is free and handy. Choices embody on-street parking on Excessive Avenue, Cross Avenue, and Queen Avenue, in addition to a number of free municipal heaps with deadlines on Spring Avenue, Cannon Avenue, and Calvert Avenue.
Chestertown makes the right addition to any Maryland Jap Shore itinerary. Take into account 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.
Last Ideas
Chestertown, Maryland, is a historic Jap 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 impartial 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 attraction 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 take pleasure in farm-to-table eating and do-it-yourself 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 do-it-yourself ice cream
- Help native and store Chestertown Farmers’ Market (Saturdays, March–December) for contemporary produce, flowers, and handmade items
For extra charming Jap Shore locations, discover Onancock, Virginia, Cape Charles, Virginia, The Oaks Waterfront Resort, and Chincoteague.
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