Plan Your Stay
- Dining & Restaurants
- Gardens
- Historic Sites/Towns
- Museums
- Outdoor Activities
- Shopping & Antiquing
- Theater Music & Art
Blue Heron Cafe
Consistently one of the best restaurants in town. Sophisticated regional American cuisine, served in a pleasant atmosphere. The oyster fritter is awesome! Open for dinner Monday through Saturday. Reservations a must on weekends. 236 Cannon Street, Chestertown – 410-778-0188
Brook’s Tavern
This 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 only take reservations for six and more. 870 High Street, Chestertown 410-810-0012
The Lemon Leaf
Intimate restaurant in the heart of Chestertown. Comfort food as well as sophisticated choices. BYOB and cash only. Cross Street, Chestertown 443-282-0004
LuLu’s Bar
Great bar food. They are open late Monday through Saturday. 337 High Street, Chestertown 410-810-2749
Inn at Osprey Point
Fantastic waterfront restaurant in Rock Hall. Wednesday—Sunday, dinner starting at 5pm 20786 Rock Hall Avenue, Rock Hall 410-639-2194
Durding’s Store
Old-fashioned soda fountain and ice cream parlor on Rock Hall’s Main Street. Definitely worth a stop. Main Street, Rock Hall 410-778-7957
Herb’s Soup & Such
Top-notch take-out food. 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
Play It Again Sam’s Coffeehouse
Besides Scottie’s Shoe Store 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. 108 S. Cross Street, Chestertown 410-778-2688
The Kitchen at Rock Hall
A wonderful little restaurant 12 miles from the inn. The food is absolutely wonderful. It is well worth the drive. They are open for breakfast, lunch and dinner, Thursday through Sunday, 8 am till 9 pm. 5757 Main Street, Rock Hall 410-639-2700
Adkins Arboretum
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
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
Chestertown
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. Stop at Scottie’s Shoe Store to pick up a newspaper and catch up on the latest gossip in town. 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.
Washington College
Explore the Chestertown campus of the 10th oldest college in the country. George Washington gave the school money, as well as his name.
Motoring
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.
Annapolis
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
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.
St.Michaels
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
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.
National Scenic Byway
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
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
St. Paul’s Cemetery
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.”
Waterfront History Tour
Chestertown, Maryland visitors are invited to experience the 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.
Winterthur, Delaware
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
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.
Waterman’s Museum
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
The Chesapeake Bay Maritime Museum
The Chesapeake Bay Maritime Museum in St. Michaels is dedicated to furthering an understanding of the culture and history of the Chesapeake Bay. This museum is an easy hour drive from Brampton Inn.
Boating
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/
Small Boat Rental
Eastern Neck Boat Rentals, Eastern Neck Island, Rock Hall. Outboard motor, rowboats, as well as fishing and crabbing supplies. 410-639-7100.
Kayaking
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
Sailing
Learn to sail on the beautiful Chesapeake Bay. Instruction available at: Maryland School of Sailing, Rock Hall, http://www.mdschool.com/ 410-639-7030.
Golf
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.
Swimming
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.
Biking
Kent County, with its gently rolling landscape and lightly traveled roads, is ideal for cycling. Please ask us for biking maps of the area.
Horseback Riding
Lovely trail rides are available at the Kent Equestrian Center http://www.kentequestrian.com/ 410-778-1881
Hunting
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
Nature Preserves and Wildlife Refuges (Hiking, Birding, etc.)
The following are all a short drive from the Brampton Inn. If you forgot your binoculars, we will be happy to lend you ours.
Eastern Neck Wildlife Refuge
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.
Sassafras River and Turners Creek Natural Resource Management Area
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.
Millington Wildlife Management Area, Maryland-Line Road, Massey
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
Wye Natural Resources Area
2,800-acre preserve on an island featuring nature trails and a wide variety of wildlife viewing. 410-827-7577.
Chesapeake Farms Wildlife Habitat
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
Farmers Market
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.
Rock Hall
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.
Prime Outlets in Queenstown
Over 45 brand name outlet stores, including Ralph Lauren, Bass, LL Bean, Nautica, Brooks Brothers, Geoffrey Beene, IZOD, Liz Claiborne, Chico, and more. 410-827-8699
Dixons Auction Sale and Farmers Market
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.
David Ferguson Oriental Rugs
David Ferguson Oriental Rugs 241 High Street, Chestertown 410-810-0603. Michael and I are very fond of oriental rugs. It’s not that we know a whole lot about collecting these pieces of art, we just like the vivid colors, the intricate details and how wonderful they look on the old wood floors of the inn. The one place we go to when we want to add to our collection is the shop of David Ferguson right here in Chestertown. David is friendly, knowledgeable and helpful. He always lets us take home a few rugs to see which one will fit best.
J.R.’s Antiques & Collectibles
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.
Mainstay, Rock Hall
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.
The Garfield Center for the Arts, Chestertown
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
Chester 5 Movie Theater
410-778-2227
Church Hill Theatre
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
Fountain Park Outdoor Concerts
Fountain Park Outdoor Concerts
For schedule of performances, click here http://www.chestertown.com/events/musicpark/
“First Friday”
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.
“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 Springs, MD
