Issues to Do in Chestertown MD: Jap Shore Exit Information
Wish to step right into a dwelling postcard? Chestertown, Maryland, has the whole lot you wish to have in a tiny coastal the town: walkable historical streets, pleasant community, distinctive eateries and indie retail outlets that really feel extra like investmrent hunts than retail.
Ancient Chestertown Maryland

Non violent waterfront perspectives alongside the Chester River in Chestertown MD with maritime appeal on complete show | Picture Higher DwellingChestertown has an enduring i’m right our must-visit checklist.
Nestled alongside the Chester River, Chestertown, on Maryland’s Jap Shore, could also be off the overwhelmed trail, however that’s precisely what makes it so particular. With fat personality and historical colonial appeal, this distinctive tiny the town could also be one among The united states’s coolest under-the-radar locations.
As soon as an noteceable port town based in 1706 and nestled alongside the banks of the Chester River, as of late you’ll be able to move via non violent brick-lined streets covered with 18th-century houses, go to historical landmarks, and store your approach via a the town that feels love it used to be adorned for a Hallmark film poised. Excluding this one is actual.
Chestertown’s downtown and historical district, indexed at the Nationwide Check in of Ancient Playgrounds, is house to Washington Faculty, the primary faculty chartered in the USA in 1782.
This pleasant the town is filled with personality. And there’s plethora to do inside of a couple of sq. blocks. In search of extra Maryland Jap Shore locations? Discover within sight St. Michaels, MD and Kent Narrows.
Issues to Do in Chestertown MD

The enduring Hebe fountain in downtown Chestertown a super spot to remains occasion exploring the historical district | Picture Higher DwellingDiscover Ancient Fountain Ground
Get started your age at Chestertown’s tiny however gorgeous Fountain Ground on the intersection of Prime and Move Streets within the middle of the town. A meeting playground during the 12 months, it’s additionally house to the Hebe Fountain, one among Chestertown’s iconic historical landmarks.
A logo of the city’s undying appeal, it’s probably the most many population art installations during the city.
Put in in 1899, product of cast-iron, painted turquoise, and entirely practical, you’ll be able to’t pass over it. Embellished fantastically with carved lions and swans, its standout detail is the Greek goddess of stripling, Hebe, who pours “ambrosia” right into a chalice on the fountain’s govern.
Talk over with the Chestertown Farmers Marketplace
Each and every Saturday from 8 to midday, right here you’ll in finding the year-round Chestertown Farmers Market, the place you’ll be able to store for native unused assemble, eggs, meat, dairy, flora, baked items, and artisan crafts.
Walk the Ancient Waterfront

Walk Chestertowns non violent waterfront boardwalk alongside the Chester River | Picture Higher DwellingIn case you’re visiting Chestertown for the primary day, don’t pass over the prospect to walk alongside its historical waterfront the place you’ll be able to experience shaded benches, river perspectives, and a tranquility playground to rest with espresso or a picnic. It’s a common birdwatching spot the place ospreys, hooded mergansers, splendid blue herons, and alternative local birds construct familiar appearances.
Docked on the Chestertown Marina, you’ll be able to additionally see the Schooner Sultana, a admirable reproduction of an 18th-century British Military vessel. It’s ceaselessly seen for population sails or dockside excursions throughout particular occasions.
Pluck a River Cruise
For extra day at the Chester River, hold a cruise on The River Packet. This 65-foot, Nineteen Twenties-style vintage yacht and excursion boat do business in weekend brunch, dinner, sundown and fickle excursions April via November that release proper from the Prime Side road Dock.
For extra waterfront eating studies, take a look at Dock and Dine Kent Narrows MD.
Attend Chestertown Fairs and Occasions
Catch a display on the Garfield Center for the Arts at the Prince Theater housed in a fantastically restored Nineteen Twenties theater or plan your go to round probably the most many every year occasions in Chestertown just like the Chestertown Jazz Festival or the Sultana Downrigging Festival every fall which is the most important annual collecting of majestic ships in North The united states mixed with bluegrass tune.
All the way through the Christmas season, come for ‘A Dickens of a Christmas’ pageant weekend the place you’ll be able to “step back into 1840s London and experience the holiday season as Charles Dickens imagined it.” Actions come with complimentary carriage rides via historical downtown, a ticketed accommodation excursion, meals distributors, an artisan village and an original Victorian tea day. Dressed in your Victorian absolute best is extremely inspired.
Get Comfortable With Pleasant Tom cats on the Cat Colloquium

Meet the resident cats within the Cat Colloquiums comfortable second floor front room | Picture Higher DwellingChestertown’s Cat Colloquium (215 Prime St #2C, Chestertown, MD 21620) run by means of nonprofit Equipment Help Inc. is a heat, welcoming and distinctive spot for cat fanatics. Right here you’ll be able to meet and snuggle up with resident cats, experience tranquility day, or chat with their pleasant volunteers.
Travel during the alley then to Stam’s Luncheonette and practice the indicators to the second one surface. The length is glorious, non violent and playful, with comfortable seating, and cat-friendly furnishings (together with a life-sized cat tree).
It’s a real invisible gem and a novel enjoy should you’re an animal lover like us and will’t go up an come across with a bushy buddy. Visiting is separate, however you’ll be able to take a look at their blog and donation options to be informed extra and help them.
In case you’re touring with 6 community or extra, make an appointment sooner than you move.
Talk over with Lockbrier Farm for Untouched Put together and Selfmade Ice Cream

Lockbriar Farms bursts with fall colours and unused seasonal assemble | Picture Higher DwellingFor a farm enjoy, an eight-minute force from downtown Chestertown, move to Lockbrier Farm to select berries, flora and pumpkins, savor farm-churned ice cream, and retain up on unused, native and seasonal assemble.
Since 1993, the Lockwood relatives—whose farming roots stretch again to the Civil Conflict—has opened the gates of Lockbrier Farms (10051 Worton Rd, Chestertown, MD 21620) to guests in the hunt for unused wind, colourful blooms, and the enjoyment of selecting their very own seasonal assemble.
All the way through our fresh fall go to, they had been brimming with mums, pumpkins, Indian corn and gourds in each and every colour. Seasonally, you’ll be able to pick out your personal culmination like strawberries, blueberries, raspberries, and blackberries. Wander via their flower and herb boxes, the place you’ll be able to abbreviate your personal to assemble your personal DIY bouquet.
After store the farm rise and retain up on unused assemble, apple cider, jams, pickled veggies, native honey, and treats like apple butter, eggs and unused cheese.
Next exploring the farm, head over to their ice cream barn for a scoop in their improbable 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 in the neighborhood sourced elements and is one of the most absolute best in Kent County.
Lockbrier Farm is seen day-to-day (climate allowing), Might via Thanksgiving, and there’s incorrect admission price. Put on boots you received’t thoughts getting grimy should you plan to discover the subjects.
The place to Store in Chestertown MD

Downtown Chestertowns brick lined streets come alive with fall appeal | Picture Higher DwellingIn case you’re uninterested in cookie-cutter vacationer traps, you’ll love Chestertown’s authentically sovereign spirit. It has 200 in the neighborhood owned retail outlets, galleries, eating places, bakeries, and cafes the place you’ll be able to hurry your day surfing home made items, uncommon books and finding one-of-a-kind reveals.
Twigs & Teacups

Twigs Teacups overflows with whimsical presents and distinctive household items | Picture Higher DwellingIn case you solely have day to move into one pack in Chestertown, construct it Twigs & Teacups (111 S Move St, Chestertown, MD 21620). Everybody we requested for native suggestions stated it used to be their favourite pack.
Manner larger than it appears to be like from the out of doors, this 2-story store is full of a curated number of whimsical and distinctive presents filled with character, together with the whole lot from unusual kitchenware and mawkish toys to in the neighborhood made items, stationery, books, puzzles, clothes and seasonal treasures. Give your self plethora of day to browse, as a result of there’s such a lot to look.
Pricing is reasonably priced, and the pleasant group of workers, which contains their resident cat Jonathan, will support you discover a distinctive present for any pace.
Chester River Wine & Cheese Co.

Sampling the improbable collection of infused olive oils and artisan meals at Chester River Wine Cheese CoA couple of doorways unwell, foodies and wine fanatics should pop into Chester River Wine & Cheese Co. (117 S Move St, Chestertown, MD 21620) This comfortable gourmand store and native favourite do business in a curated collection of wines from around the globe, and cut-to-order cheeses, charcuterie, olives, pickles, jam, snacks and area of expertise pieces. Manufacture a picnic to hurry to the riverfront or collect snacks for winding unwell after.
The group of workers listed below are satisfied to deal pairings or samples, and the store ceaselessly hosts tastings and seasonal occasions. Whether or not you wish to have a unutilized wine to attempt otherwise you’re a fromage enthusiast, this store is a scrumptious detour.
The Bookplate

The Bookplates captivating youngsterss category options whimsical reveals and uncommon titles | Picture Higher DwellingReserve fanatics must head around the road, the place they may be able to get misplaced within the cabinets at The Bookplate (112 S Move St, Chestertown, MD 21620).
This sovereign worn bookstall, which additionally sells antique prints and pottery, has a huge variety with all kinds of genres and brittle to seek out titles. The choice here’s really one among a sort, and the books are neatly arranged. If there’s one thing you wish to have however don’t see, ask the group of workers, they usually will have it invisible within the stacks or can particular situation it.
The place to Devour in Chestertown MD
With such a lot to do right here, there’s incorrect confusion you’ll get hungry. When you wish to have to devour, Chestertown has a scrumptious mixture of choices, from Chesapeake seafood, farm-to-table fare, global flavors, fickle eats and comfortable reassurance meals.
Stam’s Luncheonette

Stams Luncheonette serves nostalgic reassurance meals in a restored historical soda fountain | Picture Higher DwellingFor a fickle chew, Stam’s Luncheonette (215 Prime Side road, Chestertown, MD 21620) is a retro-style lunch counter, soda fountain and ice cream store in a restored length that used to be at the start Chester Pharmacy, opened by means of an area named John Stam about 175 years in the past.
The chant here’s nostalgic appeal serving up fickle and vintage 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 significance each and every 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 also have pints of ice cream to move. It’s a must-stop should you’re yearning comfortable reassurance meals with flavors that by no means move out of favor.
The Kitchen on the Imperial

The award profitable crab cake at The Kitchen at Imperial a must try when visiting Marylands Jap Shore | Picture Higher DwellingNext 25 years within the tech international, Chef Steve Quigg traded IT consulting for culinary creativity, and is the center in the back of The Kitchen at the Imperial (208 Prime Side road, Chestertown, MD 21620). It’s one among Chestertown’s maximum loved fickle upscale eating spots, the place each and every dish looks like a birthday celebration of the Jap Shore.
Winner of Easiest Chef at the Jap Shore 3 years in a row, Chef Steve crafts his farm-to-table menu impressed by means of what’s harvested unused from each the native farms and waterways. The menu adjustments right here ceaselessly, and the whole lot from the dinner rolls and hand-cut fries and muffins is made in-house.
A must-try here’s the Braised Lamb Shank and the signature crab truffles with completely incorrect filler, filled with unused aggregate crabmeat, completely seasoned and coupled with native assemble and house-made sauces for an increased twist. They’ve received a couple of awards for ‘Best Crab Cake’, together with honors from What’s Up? Book and Chesapeake Bay Book. Pair it with their Rosemary Grapefruit Margarita or a pitcher of wine from their intensive curated international wine list.
Unhidden for lunch, dinner and brunch on Sundays, The Kitchen on the Imperial is closed Tuesdays.
Retriever Bar

The Retriever Bars Space Burger options in the neighborhood raised grass fed pork | Picture Higher DwellingThe 21 and over Retriever Bar (337 1/2 Prime Side road, Chestertown, MD 21620) blends Chesapeake taste with a contemporary front room really feel and craft cocktails. Comfortable up in the living room, clutch a seat on the bar, which boasts probably the most intensive spirit picks on the town, together with uncommon bourbons and whiskeys.
It’s additionally Chestertown’s go-to spot for uncooked, in the neighborhood sourced Chesapeake Bay oysters, tiny 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, the whole lot is thoughtfully crafted right here.
We adore the Space Burger – a juicy double ruin burger with in the neighborhood raised, grass-fed St. Brigid’s pork, American cheese, pickles, shredded lettuce slathered with bistro sauce served on a toasted brioche roll served with fries at the aspect.
For dessert, attempt their scrumptious Apple Strudel with a scoop of creamy vanilla ice cream from Stam’s Luncheonette.
El Rancho Mexican Delicacies

El Rancho serves original Mexican road tacos with hand pressed tortillas | Picture Higher DwellingFor original Mexican flavors, El Rancho Mexican Cuisine (851 Washington Ave, Chestertown, MD 21620) is a couple of mins out of doors downtown. Opening early (6:30 AM maximum days) it’s probably the most few parks on the town the place you’ll be able to clutch a complete sizzling breakfast. The original Mexican menu do business in the whole lot from omelets and pancakes to quesadillas, burritos, fajitas, and bowls and platters.
We adore the gentle steak and flavorful Al Pastor Mexican Side road Tacos right here, which can be served in heat, hand-pressed tortillas. We additionally ordered the hen enchiladas, ½ crimson and ½ inexperienced, served with dim beans. They had been scrumptious, pleasant and actually packed some warmth.
El Rancho is fickle, reasonably priced, and best for vacationers yearning daring flavors in a laid-back surroundings. Our server, Jordan, used to be tremendous pleasant, and we’re excited to attempt the highly spiced watermelon margarita then go to. El Rancho is seen 7 days a pace for breakfast, lunch and dinner.
Fashionable Stone Day Kitchen

Untouched artisan bread cooling at Fashionable Stoneage Kitchen in downtown ChestertownModern Stone Age Kitchen (236 Cannon St, Chestertown, MD 21620) based by means of meals anthropologist and previous Washington Faculty tutor Dr. Invoice Schindler and creator of “Eat Like a Human: Nourishing Foods and Ancient Ways of Cooking to Revolutionize Your Health,” this bakery, cafe and coffee bar seen for breakfast and lunch is a one-of-a-kind safe to eat vacation spot.
Right here you’ll be able to purchase sourdough breads, bagels, croissants, pastries and scratch-made foods for breakfast and lunch ready in step with ancestral meals traditions made with elements like natural flour and lard and cooking ways like fermentation that assemble essentially the most nutrient-dense meals.
Our favourite is their scrumptious hand-rolled sourdough pretzels, which promote out speedy. You’ll additionally clutch refrigerated ready meals to move like fermented veggies, yogurt, cheeses and house-made liverwurst.
Bakery seating is to be had within, nevertheless it fills up briefly. When it’s heat, head to their nice-looking yard out of doors. In case you’re , test their calendar of classes to be informed historic meals prep abilities like sourdough baking and fermentation.
The place to Keep in Chestertown MD

Brampton 1860s admirable Nineteenth century structure shines towards a starlit Jap Shore sky | Picture Higher DwellingBrampton 1860
Keep longer and get up at a sumptuous historical 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 indexed at the Make a selection Registry, Brampton 1860’s (25227 Chestertown Street Chestertown, MD 21620) completely restored historical structure, still environment, original hospitality and a spotlight to property have earned it govern rankings and a faithful following.

Within Marleys Cottage at Brampton 1860 | Picture Higher DwellingGet up in probably the most seven thoughtfully appointed rooms and suites in the primary accommodation or six personal cottages scattered during the trait. Each and every has sumptuous facilities like spa tubs, fireplaces, sumptuous Comphy™ linens, canny TVs and separate Wi-Fi.
Each and every morning, experience a freshly ready multi-course gourmand à los angeles carte breakfast of their unclouded eating room with menu choices like Lemon Croissant French Toast and Apple Pancakes that fluctuate day-to-day. Have it served on their sprawling porch, deck or breakfast room. Seasonal elements, do-it-yourself pastries, and heat hospitality are all the time integrated.

Brampton 1860s gourmand à los angeles carte breakfast options day to day specials like fluffy pancakes | Picture Higher DwellingRight through the age, support your self to a collection of baked items and next go back within the afternoon for his or her Afternoon Tea for scrumptious tiny plates, dessert, complimentary wine, espresso and tea. Next breakfast, go to their flock of chickens and next move via Brampton’s formal boxes with fruit bushes, trails and wild meadows that draw in birds, butterflies, and tiny flora and fauna.
At night time, curl up with a hold by means of the fireside, do a puzzle within the library or experience a pitcher of wine of their bar and front room. We adore enjoyable by means of the out of doors firepit the place we will see heaps of stars. Don’t be shocked if their cat Squeaky comes by means of to stock you corporate.

Curl up with a hold in Brampton 1860s inviting library by means of the fireside | Picture Higher DwellingWith customized provider, Brampton 1860 do business in a novel enjoy that feels each undying and inviting. And also you’ll have the most productive of each worlds: lodging at a calm, sumptuous, historical geographical region property and the ease of Chestertown’s indie retail outlets, galleries, and eating places simply 5 mins away. Brampton is adults-only and pet-friendly. EV charging stations are to be had. For the most productive charges, book direct.
💡 Learn our entire Brampton 1860 Review and uncover Fall Fun at Brampton 1860 for seasonal actions.
Attending to Chestertown, MD
On Maryland’s Jap Shore in Kent County, Chestertown is:
- 1 presen from Wilmington, DE
- 1.5 hours from Baltimore
- 1.5 hours from Washington, D.C.
- 1.5 hours from Philadelphia
Using: In case you’re using, you’ll be able to achieve Chestertown by the use of Course 213 or Course 301, whether or not you’re coming from the north or south.
Aviation: The later main airport is Baltimore/Washington Global Thurgood Marshall Airport (BWI), about 70 miles away. From BWI, you’ll be able to hire a automotive or hurry a go back and forth provider to Chestertown.
Boating: Dock on the Chestertown Marina. Test slip rates here and make contact with 410-778-3616 to hold your brief slip.
Parking: As soon as in Chestertown, parking is separate and handy. Choices come with on-street parking on Prime Side road, Move Side road, and Queen Side road, in addition to a couple of separate municipal so much with day limits on Spring Side road, Cannon Side road, and Calvert Side road.
Chestertown makes the easiest addition to any Maryland Jap Shore itinerary. Believe it as a part of your day trips from Washington DC or discover extra with the best day trips from Philadelphia for nature lovers.
Ultimate Ideas
Chestertown, Maryland, is a historical Jap Shore the town recognized for its brick-lined streets, colonial structure, and scenic riverfront.
Based within the 1700s, it do business in an enthralling depart with over 200 sovereign retail outlets, galleries, and cafes, with a number of issues to do and occasions.
It makes the easiest fleeing or age shuttle if you wish to find a distinctive vacation spot with heaps of appeal and with out the crowds.
For a calm and opulent retreat a couple of mins from downtown Chestertown, keep at Brampton 1860.
Chestertown is compact however stuffed with issues to do!
Whether or not you’re making plans a romantic weekend, a solo depart, or a family-friendly journey, Chestertown do business in one thing for everybody:
- Historical past fanatics can discover colonial structure and heritage websites
- Foodies can experience farm-to-table eating and do-it-yourself ice cream
- Browse indie boutiques for distinctive reveals
- Discover the historical waterfront or hurry a river cruise
- Pick out your personal berries at Lockbriar Farms, next cool off with do-it-yourself ice cream
- Help native and store Chestertown Farmers’ Marketplace (Saturdays, March–December) for unused assemble, flora, and home made items
For extra captivating Jap Shore locations, discover Onancock, Virginia, Cape Charles, Virginia, The Oaks Waterfront Hotel, and Chincoteague.
Higher Dwelling makes use of associate hyperlinks. In case you construct a purchase order via them, we might obtain a tiny fee (for which we’re deeply thankful) without charge to you.
Source link

