Bob’s guidebook
Sightseeing
Living working historic town on the Chester River. Tree lined brick sidewalks with unique shopping and dining.
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Chestertown
Living working historic town on the Chester River. Tree lined brick sidewalks with unique shopping and dining.
Sultana Education Foundation
200 S Cross StSmall liberal art college. Founded in 1782 and the only college George actually permitted to use his name.
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Washington College
300 Washington AveSmall liberal art college. Founded in 1782 and the only college George actually permitted to use his name.
Chestertown Marina LLC
207 S Water StNewly updated and renovated
Runs along the river front. Wonderful colonial architecture. Hynson Ringgold house is currently the president of Washington College's residence. Custom House, Widehall, and the River house are but a few of the historic homes.
South Water Street
South Water StreetRuns along the river front. Wonderful colonial architecture. Hynson Ringgold house is currently the president of Washington College's residence. Custom House, Widehall, and the River house are but a few of the historic homes.
To get the real feel of the Eastern Shore
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Eastern Neck National Wildlife Refuge
1730 Eastern Neck Island RdTo get the real feel of the Eastern Shore
The last of the watermen still work out of this quaint village. Now home to marinas. Interesting museum.
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Rock Hall
The last of the watermen still work out of this quaint village. Now home to marinas. Interesting museum.
One of the only public beaches in the area. Nice wide beach with good facilities. About 25 minute drive
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Betterton Beach
One of the only public beaches in the area. Nice wide beach with good facilities. About 25 minute drive
Turner's Creek Park and Sassafras Natural Resource Management Area lie side-by-side along the Eastern Shore's Sassafras River. The 143-acre park and the nearby natural harbor of Turner's Creek was once the site of a thriving local shipping port, disbursing agricultural goods throughout the Bay region.
Now the tranquil harbor is now home to a half dozen crabbing and fishing boats. A granary still stands on the site where an earlier commissary shipped supplies to Washington's troops at Valley Forge. The Kent Museum, housing many artifacts from the Kent County of bygone years, stands a few hundred yards up the hill from the Granary and Landing.
Spectacular views open at every turn along the trails and old roads of the adjacent Sassafras Natural Resource Management Area. Fresh and saltwater ponds, wooded ravines, farm fields, a variety of forest stands and the river itself create prime habitat for viewing waterfowl and many other species
Turners Creek Landing
Turners Creek RoadTurner's Creek Park and Sassafras Natural Resource Management Area lie side-by-side along the Eastern Shore's Sassafras River. The 143-acre park and the nearby natural harbor of Turner's Creek was once the site of a thriving local shipping port, disbursing agricultural goods throughout the Bay region.
Now the tranquil harbor is now home to a half dozen crabbing and fishing boats. A granary still stands on the site where an earlier commissary shipped supplies to Washington's troops at Valley Forge. The Kent Museum, housing many artifacts from the Kent County of bygone years, stands a few hundred yards up the hill from the Granary and Landing.
Spectacular views open at every turn along the trails and old roads of the adjacent Sassafras Natural Resource Management Area. Fresh and saltwater ponds, wooded ravines, farm fields, a variety of forest stands and the river itself create prime habitat for viewing waterfowl and many other species
Food scene
Great food in spite of the chef's attitude. (yea he is a friend).
Open Monday, Tuesday, Wednesday & Thursday 5-9. Friday & Saturday 11:30-9pm Sunday 10-9. 410-778-5000
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The Kitchen at the Imperial
208 High StGreat food in spite of the chef's attitude. (yea he is a friend).
Open Monday, Tuesday, Wednesday & Thursday 5-9. Friday & Saturday 11:30-9pm Sunday 10-9. 410-778-5000
Due to a fire on 1/12/22 and structural issues it is closed for repairs indefinitely.
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98 Cannon Riverfront Grille
98 Cannon StDue to a fire on 1/12/22 and structural issues it is closed for repairs indefinitely.
baguettes baked fresh daily. Try the everknott or sinbun. Closed Monday and Tuesday
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Evergrain Bread Company
201 High Stbaguettes baked fresh daily. Try the everknott or sinbun. Closed Monday and Tuesday
Local coffee shop. The norwegian is my favorite.
8-3 everyday.
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Play It Again Sam
108 S Cross StLocal coffee shop. The norwegian is my favorite.
8-3 everyday.
Consistently great food. Open 11-8 Monday-Thursday 11-8:30 Friday Saturday 11:30-8 Sunday
410-778-5360
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Luisa's Cucina Italiana
849 Washington AveConsistently great food. Open 11-8 Monday-Thursday 11-8:30 Friday Saturday 11:30-8 Sunday
410-778-5360
A college favorite
Open daily 11:30-2 and 5-8 (9 on Friday Saturday)
410-778-6688
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Cafe Sado
205 Tackle CirA college favorite
Open daily 11:30-2 and 5-8 (9 on Friday Saturday)
410-778-6688
Great wood fired pizza, The Poblano Popper is a must have as an appetizer and my favorite pies are Water Street or Spring Street. Flank salad is always a go too as well.
Only open Thursday & Friday 5-9pm - Saturday 12-9pm
443-282-0163
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BAD Alfred's Distilling
323 High StGreat wood fired pizza, The Poblano Popper is a must have as an appetizer and my favorite pies are Water Street or Spring Street. Flank salad is always a go too as well.
Only open Thursday & Friday 5-9pm - Saturday 12-9pm
443-282-0163
This is the place that when my kids visit they have to go to eat. (they currently live in Reading, Chicago, Dallas, and London)
Tuesday -Sunday 11-9 closed Monday
410-778-5900
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Procolino's Pizza
711 Washington AveThis is the place that when my kids visit they have to go to eat. (they currently live in Reading, Chicago, Dallas, and London)
Tuesday -Sunday 11-9 closed Monday
410-778-5900
Eat crabs on their deck on the harbor in Rock Hall
hours vary by season
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Waterman's Crab House
21055 W Sharp StEat crabs on their deck on the harbor in Rock Hall
hours vary by season
fresh seafood to go.... hands down the very best crabcakes that you can take home, bake and call your own.
closed Sunday and Monday open all other days 11-6
410-758-3933
If traveling from the south or west call ahead and pick some up coming or going.
Bay Shore Steam Pot
111 E Water Stfresh seafood to go.... hands down the very best crabcakes that you can take home, bake and call your own.
closed Sunday and Monday open all other days 11-6
410-758-3933
If traveling from the south or west call ahead and pick some up coming or going.
Great local wine, my fav is Tinto. Include a small plate or two and it's heaven.
Currently open Thursday - Friday 4-9pm - Saturday 12-9 Sunday 11-3
410-390-9921
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Casa Carmen Wines
312 Cannon StGreat local wine, my fav is Tinto. Include a small plate or two and it's heaven.
Currently open Thursday - Friday 4-9pm - Saturday 12-9 Sunday 11-3
410-390-9921
The oyster fritter is a must.
Open Tuesday - Thursday11-8 Friday 11-9 Saturday 12-9
410-778-3663
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Uncle Charlie's Bistro
834 High StThe oyster fritter is a must.
Open Tuesday - Thursday11-8 Friday 11-9 Saturday 12-9
410-778-3663
Recently renovated. Home made ice cream hand dipped. Great Lunch
Open Wednesday-Friday 11-4 Saturday 9-4
Sunday 11-4
410-885-6722
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Stam's Luncheonette
215 High StreetRecently renovated. Home made ice cream hand dipped. Great Lunch
Open Wednesday-Friday 11-4 Saturday 9-4
Sunday 11-4
410-885-6722
Lively atmosphere with a large deck and good food, of course crabs. Local favoite
closed Monday & Tuesday other days 11-8 to 9 on fri sat
(410)-639-9996
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Harbor Shack
20895 Bayside AveLively atmosphere with a large deck and good food, of course crabs. Local favoite
closed Monday & Tuesday other days 11-8 to 9 on fri sat
(410)-639-9996
Located in historic downtown Chestertown in and around Fountain Park
Every Saturday 7-12
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Marylands Chestertown Farmers & Artisans Market
118 North Cross StreetLocated in historic downtown Chestertown in and around Fountain Park
Every Saturday 7-12
Buddys Crabs
2756 Church Hill RoadFor fresh crabs to go.
410-758-0311
Chestertown's newest and fanciest restaurant.
Open Wednesday, Thursday, Friday, & Saturday. 5-9
443-282-9797
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Watershed Chestertown
337 High StreetChestertown's newest and fanciest restaurant.
Open Wednesday, Thursday, Friday, & Saturday. 5-9
443-282-9797
A local favorite for fresh seafood and crabs. Open Monday - Thursday 7am-8pm Sunday 7am - 7pm
Crabs to go
Ford's Seafood
A local favorite for fresh seafood and crabs. Open Monday - Thursday 7am-8pm Sunday 7am - 7pm
Crabs to go
Clark Seafood
23242 Handy Point Rdseafood market... favorite for crabs to go
Shopping
Their auctions are now online on every other Wednesday at www.crumptonauctions.com. You can go on Monday and Tuesday to browse the selections. (every other week) Only 3 miles from the house
Dixon's Furniture Auction
2017 Dudley Corner RdTheir auctions are now online on every other Wednesday at www.crumptonauctions.com. You can go on Monday and Tuesday to browse the selections. (every other week) Only 3 miles from the house
The Finishing Touch
311 High StThis is my business.... please visit and say hi.
Walnut & Wool
321 High StVery cool business , not to be missed
Fun store with a bit of everything. Kids love this place. Currently being renovated with a "pop up" location on High Street
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Twigs & Teacups
111 S Cross StFun store with a bit of everything. Kids love this place. Currently being renovated with a "pop up" location on High Street
Mimi's Closet
307 High StBoutique with lots of variety. Women's clothing.
Houston's Dockside Emporium
315 High StClothing and lots of local themed items.
Find that un-findable book you are looking for or didn't know you were looking for
112 S. Cross St.
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Book Plate
112 S Cross StFind that un-findable book you are looking for or didn't know you were looking for
112 S. Cross St.
Chestertown's premier Art Gallery
Also, check out it's sister Gallery on South Cross St. named Create.
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MassoniArt Gallery
203 High StChestertown's premier Art Gallery
Also, check out it's sister Gallery on South Cross St. named Create.
Grocery
Cross Street Food and Garden
105 W Cross StFresh local product
Chestertown Marina LLC
207 S Water StClassic Health food store
Food Lion
31810 River RdMy prefered chain food store
ACME Markets
711 Washington Ave
Redner's Markets
2500 S Dupont HwyOffers almost anything you could want at reasonable prices
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Dollar General
106 Philosophers TerraceOffers almost anything you could want at reasonable prices
adult drinks
shanty bar
21085 Tolchester Beach RdBeach Bar with the best sunsets & entertainment.
Open in season
410-778-1400
Zelda's Speakeasy - my favorite place for a drink. Tell Jeff the amazing bartender and owner that I sent you. Only open Thursday & Fridays and assorted special days, if the green light is on he is open. Not to be missed
108 S Cross St
108 South Cross StreetZelda's Speakeasy - my favorite place for a drink. Tell Jeff the amazing bartender and owner that I sent you. Only open Thursday & Fridays and assorted special days, if the green light is on he is open. Not to be missed
The Retriever Oyster Bar. Thursday is "Buck a Shuck" night. Drinks for every palate with great food - Open Tuesday - Saturday.
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LTO
337 1/2 High StThe Retriever Oyster Bar. Thursday is "Buck a Shuck" night. Drinks for every palate with great food - Open Tuesday - Saturday.
Consigli per viaggiatori
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Saturday farmers market - 8-12am
Downtown Chestertown, streets close and local produce and products
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For the river water quality check with Shore Rivers
Search their name .org/swim and Look under Chester River for Crumpton landing. It is about 1/2 mile up river (to the east) from the house