Plan Your Stay
- Dining & Restaurants
- Doing Nothing
- Historic Sites/Towns
- Outdoor Activities
- Shopping & Antiquing
- Theater Music & Art
The Chesapeake Bay area is home to hundreds of bird species. Some of the areas most recognizable visitors are Bald Eagles, Osprey, Tundra Swans, Canada Geese and Snow Geese.
Eastern Neck Wild Life Refuge is a only 20 min. from our Chestertown Inn.
At the Brampton Bed and Breakfast Inn we have hosted among many species Wood Ducks, Egrets, Owls, Cedar Waxwing, Cardinals, Finches, Humming Birds and Buzzards.
Check out this Osprey Cam.
Brook’s Tavern is casual restaurant is housed in a restored old mill and is simply awesome. The food is imaginative, beautifully presented, and the restaurant is less than a mile from the inn. They take reservations for six and more. 870 High Street, Chestertown 410-810-0012
The Front Room at the Imperial Hotel is open for lunch Tuesday – Friday and dinner Tuesday -Saturday 4:00 pm to 9:00 pm and on Sunday 4:00 pm to 8:00 pm. The cocktails are creative, the food good and the ambience elegant. Located on 208 High Street next door to the Garfield Center of the Arts in the historic district of Chestertown. Reservations are recommended. 410-778-5000
A wonderful little restaurant 12 miles from the inn. The food at the Kitchen is absolutely fantastic. It is well worth the drive. They are open for lunch and dinner Thursday through Monday, 11:30 am till 9 pm. Breakfast Saturday and Sunday starting at 8 am. They close each afternoon from 3 pm til 5 pm. 5757 Main Street, Rock Hall 410-639-2700
The Inn at Osprey Point has a fantastic waterfront restaurant in Rock Hall. Wednesday—Sunday, dinner starting at 5 pm 20786 Rock Hall Avenue, Rock Hall 410-639-2194
The Evergrain Bread Company is a wonderful bakery and cafe located on High Street. They offer some of the best coffee in town. They offer soups and great sandwiches for lunch. 201-203 High Street, Chestertown, MD 21620 410 778-3333 Wed – Sun 7:00 AM – 5:00 PM Closed Monday & Tuesday
The Lemon Leaf is very popular spot among Chestertown locals as well as inn guests. Comfort food as well as sophisticated choices. Great pub with lounge. 337 High Street, Chestertown 443-282-0004
Uncle Charlie’s is the place to go for a casual meal. Favored by the locals it offers a homey meals at an affordable price and friendly service. 834B High Street in Chestertown 410-778-3663
Herb’s Soup and Such is a top-notch take-out food place. Fresh, local ingredients, nicely prepared. Open Monday through Friday for breakfast and lunch, 7:30 to 3 p.m. 827 High Street, Chestertown 410-778-9727
One of the best kept secrets during the summer is the very casual Sandbar at Rolph’s Wharf. It’s an outdoor bar, open on weekends, with the best view of the Chester River. They offer cold beer and simple snacks. It is the best place to enjoy the sunset.
This is the best place to brush up on local gossip. They also serve great espresso, cappuccino and a limited lunch menu which can be enjoyed al fresco during the warmer months. 108 S. Cross Street, Chestertown 410-778-2688
This place has been around for a long time and can be outstanding. It’s been a bit hit and miss lately. Open for dinner Monday through Saturday. Reservations a must on weekends. 236 Cannon Street, Chestertown – 410-778-0188
Old-fashioned soda fountain and ice cream parlor on Rock Hall’s Main Street. Open during the summer months. Definitely worth a stop. Main Street, Rock Hall 410-778-7957
If you are looking for a place to relax without the pressure of doing something look no further than the Brampton Bed and Breakfast Inn. Our rooms are exceptionally large and spacious and perfect for lounging about. They all have sitting areas, good lighting, TVs for movie watching and en-suite bathrooms.
Front Porch Surfing is a relaxing activity found abundantly on Brampton’s massive wrap-around front porch from April through October, weather permitting. Bring a book, iPad, Kindle etc. Grab a glass of lemonade and pick your favorite spot. Read, snooze, sip, repeat as needed. There is no minimum or maximum time. We recommend you do it as long as you want!
Adkins Arboretum is a 400-acre native garden and preserve on Maryland’s Eastern Shore dedicated to promoting the appreciation and conservation of the region’s native plants. It is one of Michael and Danielle’s favorite places to walk and only 30 minutes from the inn. 410-634-2847
Longwood Gardens, Kennett Square, PA. The world’s premier horticultural display garden is about 1-1/2 hours away from our Chestertown Inn and offers 1,050 acres of gardens, woodlands, and meadows, 20 outdoor gardens, 20 indoor gardens within 4 acres of heated greenhouses, 11,000 different types of plants and spectacular fountains. 610-388-1000
Our garden is lovingly tended by Manick and Michael. Between the two of them they weed, plant, transplant and cut the grass. Not a small task considering the inn sits on twenty acres, four of which are on the National Register of Historic Places.
Manick is in charge of the flowers and perennials.
Michael has taken on the vegetable garden. He planted lettuce, eggplants, tomatoes, cabbages, beans and two beds of herbs. We will be using all of it at the inn. I promise not to serve cabbage and string beans for breakfast but we will use it for coleslaw at the crab feasts in the summer.
Together they take turns cutting the grass and look after our magnificent English box woods. Snow storms and Hurricane Irene have been tough on them lately. With the right care they are recovering slowly and the scent is still as enthralling as it always has been.
This quintessential colonial village is full of historical attractions and is a great town to explore on foot. For a wonderful historical/architectural tour of Chestertown, Maryland, click here http://www.chestertown.com/places/index.php. You can plan on taking a leisurely walk through one of only 6 “Royal Ports of Call” during colonial times, with the help of the Chestertown walking map. Enjoy the 2nd highest concentration of 18th century houses in the state, after Annapolis. Stroll past the beautiful homes along the Chester River. Chestertown was named the Mid-Atlantic’s most charming town by Washingtonian Magazine.
A wonderful source for local news is the Chestertown Spy. The Chestertown Spy is an internet news source for the Chester River community on the Eastern Shore of Maryland. It is published in Chestertown Monday through Thursday.
Explore the Chestertown campus of the 10th oldest college in the country. George Washington gave the school money, as well as his name.
Explore Maryland’s smallest county by car and enjoy the beauty of this rural landscape, with waterways, charming towns and animals grazing in the fields of working farms. Ask us for the Kent County Driving Tour and our own itinerary with many points of interest before heading out.
The capital of Maryland and a historic treasure is just an hour’s drive away. Visit the Naval Academy or take a boat ride on the Severn River. Walking tours, boat tours and bike tours are all available.
Easton, about 30 miles from the inn, was named “the 8th Best Small Town in America” and is an arts and cultural center, with lots of shopping and many things to do.
About an hours drive South of our Eastern Shore Inn in St. Michaels is the home of the Chesapeake Bay Maritime Museum http://www.cbmm.org/. The Museum is a non-profit organization dedicated to furthering an understanding of the culture and history of the Chesapeake Bay. It is well worth a visit.
Tilghman Island is a true working waterman’s village, with excellent fishing and fresh seafood everywhere. It is the home of the last commercial sailing fleet in North America, located in Dogwood Harbor.
Maryland’s National Scenic Byway, Route 213, bisects Kent County from the northern Sassafras River border to the southern Chester River border and includes Routes 20 and 445. For detailed driving instructions, map and info, click here http://www.byways.org/explore/byways/2261/travel.html
The Geddes-Piper House is the seat of the Historical Society of Kent County. This beautifully restored 18th century building is open to the public. 410-778-3499
The late actress Tallulah Bankhead, is buried at St. Paul’s Cemetery, a gorgeous spot, not very far from the inn. She was known for her outrageous behavior and supposedly said: “The only thing I regret about my past is the length of it. If I had to live my life again I’d make all the same mistakes – only sooner.”
Chestertown, Maryland visitors are invited to experience Washington College’s Starr Center’s new multimedia tour of the Chestertown waterfront. The audio-guided tour, “History on the Waterfront: a Journey Into Chestertown’s Past,” is available Friday afternoons from 12:00 to 4:00 p.m. and Saturdays from 11:00 a.m. to 4:00 p.m., with the exception of college holidays. Reservations to take the tour at other times may be made by calling 410-810-7161. Tours begin at the Custom House, 101 S. Water St. in Chestertown.
Visit this world-famous DuPont Estate, just 1-1/2 hours away, with beautiful gardens and the most spectacular collection of American furniture and decorative arts anywhere in the world. 800-448-3883
Kent Museum was organized in the 1960’s to preserve Kent County’s rural heritage. Local farming families have donated agricultural equipment and household items from the past. 410-348-5239.
This museum is dedicated to the Watermen of the Chesapeake Bay whose heritage plays a great role in the history of Maryland’s Eastern Shore. 410-778-6697
You can enjoy Day and Sunset Cruises with Captains Mark and Suzanne Einstein. Our guests rave about their experience on the “Blue Crab” Click here for details http://www.bluecrabcharters.com/
Eastern Neck Boat Rentals, Eastern Neck Island, Rock Hall. Outboard motor, rowboats, as well as fishing and crabbing supplies. 410-639-7100.
Brampton is very close to several landings ideal for kayaking on the Chester River as well as the Chesapeake Bay. Bring your kayaks and explore one of the nation’s most interesting estuaries. If you prefer a guided tour try Chester River Kayak Adventures http://www.crkayakadventures.com/ 410-639-2001
Learn to sail on the beautiful Chesapeake Bay. Instruction available at: Maryland School of Sailing, Rock Hall, http://www.mdschool.com/ 410-639-7030.
You can use our golfing privileges at the Chester River Yacht and Country Club http://www.crycc.org/ located less than a mile from the inn. Tee time reservations are normally not required. However, during the summer months, it’s prudent to inquire if events are planned at the club that would prevent you from playing golf. (A group minimum of three or more is needed to play on Saturday mornings.) 410-778-1372. A greens fee applies.
You may use the pool at the Chester River Yacht and Country Club http://www.crycc.org/ or the Rock Hall Yacht Club http://www.rockhallyachtclub.org/. We prefer the pool at the Rock Hall Yacht Club. The scenery is gorgeous but it’s a bit further away from our Chesapeake Bay Inn.
Swimming from a sandy beach is available at the 3.2 acre Betterton Beach County Park 12 miles north of the inn. Changing rooms and restrooms are available on the premises. Betterton was once a thriving 19th Century Victorian resort with its own steamboat landing on the Chesapeake Bay. 410-778-1948.
Kent County, with its gently rolling landscape and lightly traveled roads, is ideal for cycling. Please ask us for biking maps of the area.
Riding lessons are available at the: Worthmore Equestrian Center
11570 Still Pond Road, Worton, MD 21678 ~ (410) 348-2055
Waterfowl hunting is synonymous with Kent County, the Winter home of the largest Canada geese migrating population on the Eastern Flyway. Canada geese, snow geese, ducks, doves, pheasants, quails can all be hunted through various outfitters. Ask Danielle or Michael for contact information.
We have been welcoming hunters since 1987 offering breakfast as early as 4:30 AM!
The following are all a short drive from the Brampton Inn. If you forgot your binoculars, we will be happy to lend you ours.
2,300-acre island habitat featuring nature trails, picnic areas, bald eagles, migratory waterfowl, and more. It is a good cycling destination from the Brampton Inn. 410-639-7056.
1,000 acres of farmland, mature forests, sandy beach, tidal ponds and marshland. Nature trails, open fields, and a waterfront bluff overlooking the Sassafras River. See waterfowl, songbirds, eagles, deer, beaver, muskrat, raccoon, woodchuck. 410-778-1948.
4 ponds stocked with bass and bluegill within 3,800 acre preserve. Hiking, bird and wildlife watching, mountain biking. See woodpeckers, woodcocks, scarlet tanagers, and beaver. 410-928-3650
2,800-acre preserve on an island featuring nature trails and a wide variety of wildlife viewing. 410-827-7577.
Chesapeake Farms Wildlife Habitat is a 3,300-acre preserve with a wonderful self-guided driving tour and is home to a variety of birds, deer, fox, bald eagle etc. 410-778-8400. 7319 Remington Drive, Chestertown
Do not miss the Chestertown Farmers Market in Fountain Park http://www.chestertown.com/market/, Saturdays at 9 am, April through December. You will find wonderful produce, baked goods, soaps, plants and crafts.
Hop aboard the convenient trolley operating between Chestertown and Rock Hall 410-639-7996. Shops in Rock Hall include gift shops, antiques shops, galleries, artisan and craft studios in Oyster Court, a 1930′s ice cream parlor, and restaurants. 410-778-0416.
Over 45 brand name outlet stores, including Adidas, Banana Republic, Nautica, JCrew, Brooks Brothers, Levi’s, Chico, and more. 410-827-8699
Year-round auction with thousands of items up for bid. Antiques, furniture, glassware, and other assorted treasures can be found here. Held every Wednesday from 9:00 a.m. till 5:00 p.m. Route 544, Crumpton 410-928-3006.
We have found many of the pieces used throughout the inn at the J.R.’s Antiques formerly known as the Chesapeake Antiques Center. Antiques and collectibles are housed in this enormous warehouse. Open every day from 10:00 a.m. till 5:00 p.m. J.R.’s is located approx. 40 min. from the inn on Rt. 301.
Treasures Re-Found is a fantastic antiques store tucked away behind the main street in Chestertown, MD. Just looking at the unassuming store front you would never believe what is hiding behind those doors. Well worth a trip if you are interested in “Old Stuff”!
The Mainstay is a warm friendly place with great sound and sight lines. With only 120 seats, there’s not a bad one in the house. It’s a listening room that’s almost as comfortable as your living room. Beer, wine and soft drinks are available. Our audiences range from local Rock Hallers to those who find their way here from Philadelphia, Annapolis, Baltimore, Washington DC and beyond. 410-639-9133.
A wonderful old vaudeville theater, renovated and now presenting a wide range of concerts and live performances of jazz, live theater, dance, as well as films. 410-810-2060.
Chester 5 Movie Theater
Performing arts center in a sleepy Eastern Shore town. Live theater and musical productions presented in this beautifully-restored art deco theater, on the national register of historic places. 410-758-1331
A monthly celebration in Chestertown. Every first Friday of the month shops and galleries stay open late and the local artists are available to meet with the public. Several of the shops serve wine and cheese plates. There is also a small theater that hosts local musicians.
Find out from the insiders about the top things to do in Maryland and on the Chesapeake Bay. Join us in our beautiful Eastern Shore bed and breakfast for a getaway to remember.
“It may look like a blah Winter day, but the warmth and comfort of the cottage has made this a day in heaven.”
~ RM and Terry, Silver Spring, MD