Food scene
The Chesapeake Inn has both a more formal setting as well as more casual outdoor seating.
40 locals recommend
Chesapeake Inn Restaurant & Marina
605 2nd StThe Chesapeake Inn has both a more formal setting as well as more casual outdoor seating.
Schaefer's Canal House
208 Bank StSchaeffer's Canal House also has a great outdoor setting.
Deep Blue Restaurant
14028 Augustine Herman HighwayBeautiful overlook of the Sassafrass River
If you aren't as concerned with being near the water, La Bance in Middletown is delicious! It is about 20 minutes away.
La Banca
1 West Main StreetIf you aren't as concerned with being near the water, La Bance in Middletown is delicious! It is about 20 minutes away.
There is a beautiful winery right across the water from the house (5 minute drive).
26 locals recommend
Chateau Bu-De, LLC Bohemia Manor Farm
237 Bohemia Manor Farm LnThere is a beautiful winery right across the water from the house (5 minute drive).
There is a second winery also close by that often has events. They list events on their website regularly.
16 locals recommend
Broken Spoke Winery
942 Glebe RdThere is a second winery also close by that often has events. They list events on their website regularly.
Cafe on the Bay
19 Bohemia AveA cute coffee shop in Chesapeake City to check out.
Need to pick up a bottle of wine or other libations? Check out Beach House about 10 minutes away. They also have a limited supply of groceries if you need to pick something small up.
The Beach House Wine & Spirits
1880 Crystal Beach RoadNeed to pick up a bottle of wine or other libations? Check out Beach House about 10 minutes away. They also have a limited supply of groceries if you need to pick something small up.
Pizza House
122 W Main StPizza for pick up or delivery
Prime 225
225 Bohemia AveSteak house in Chesapeake City
Redner's Warehouse Markets
311 Augustine Herman HwyThis full service grocery store is about 15 minutes away.
They have one of the best espresso martinis around! Like most places in Chesapeake City, upstairs is more formal while downstairs (called Hole in the Wall here) is more casual.
16 locals recommend
The Bayard House Restaurant
11 Bohemia AveThey have one of the best espresso martinis around! Like most places in Chesapeake City, upstairs is more formal while downstairs (called Hole in the Wall here) is more casual.
Not quite as busy as Chesapeake City places but still a great view of the water.
23 locals recommend
Fish Whistle
100 George StreetNot quite as busy as Chesapeake City places but still a great view of the water.
Don't miss your chance to visit the Amish store right down the road from the house! An easy 5-minute walk will give you access to homemade baked goods, local produce, and other food items they add as they ramp up their options. The store is currently open Thurs-Sat.
1444 Glebe Rd
Don't miss your chance to visit the Amish store right down the road from the house! An easy 5-minute walk will give you access to homemade baked goods, local produce, and other food items they add as they ramp up their options. The store is currently open Thurs-Sat.
If you want to explore a local brewery, Volunteer Brewing Co in Middletown should be on your list. They often have food trucks and live music and it's set in the older part of Middletown that still has a lot of character.
Volunteer Brewing Company
If you want to explore a local brewery, Volunteer Brewing Co in Middletown should be on your list. They often have food trucks and live music and it's set in the older part of Middletown that still has a lot of character.
City/town information
A cute town 10 minutes north of the house that has shops and restaurants to meander through.
33 locals recommend
Chesapeake City
A cute town 10 minutes north of the house that has shops and restaurants to meander through.
This town in Delaware is about 20 mintues away and has all the large shops and stores you could want (Home Depot. Home Goods, Chick-Fil-A, etc). Delaware is a sales tax free state!
7 locals recommend
Middletown
This town in Delaware is about 20 mintues away and has all the large shops and stores you could want (Home Depot. Home Goods, Chick-Fil-A, etc). Delaware is a sales tax free state!
Chestertown is about a 35-minute drive from the house and is located on Maryland’s Eastern Shore on the banks of the Chester River. Established in 1706, this small colonial town encompasses the arts, the environment, and history.
It is a walkable historic river town with plenty of shopping, galleries, and dining to keep you busy. Check out their robust Events page during your stay.
It is also the home to Washington College, the first college chartered in the sovereign United States of America.
Maryland 213
Chestertown is about a 35-minute drive from the house and is located on Maryland’s Eastern Shore on the banks of the Chester River. Established in 1706, this small colonial town encompasses the arts, the environment, and history.
It is a walkable historic river town with plenty of shopping, galleries, and dining to keep you busy. Check out their robust Events page during your stay.
It is also the home to Washington College, the first college chartered in the sovereign United States of America.
Rock Hall is about a 45-minute drive from the house. Beginning as a small harbor town, it has been an important part of the historical fabric of the Eastern Shore. Fishing, boating, hunting, birdwatching, biking, walking, sunning, beachcombing, playing, or just sitting back with your favorite drink – Rock Hall has it all!
There are many ways to get on the water in Rock Hall: https://www.rockhallmd.com/visitors/pages/boating
Maryland 445
Rock Hall is about a 45-minute drive from the house. Beginning as a small harbor town, it has been an important part of the historical fabric of the Eastern Shore. Fishing, boating, hunting, birdwatching, biking, walking, sunning, beachcombing, playing, or just sitting back with your favorite drink – Rock Hall has it all!
There are many ways to get on the water in Rock Hall: https://www.rockhallmd.com/visitors/pages/boating
Sightseeing
This is a paved trail that runs beside the canal that is a great place to walk, run, or ride bike.
Ben Cardin C&d Canal Recreation Trail
This is a paved trail that runs beside the canal that is a great place to walk, run, or ride bike.
M/V Bay Breeze
208 Bank StThis is another option for a boat tour out of Chesapeake City.
Mount Harmon Plantation offers tours of this historical site.
9 locals recommend
Mount Harmon Plantation
600 Mt Harmon RdMount Harmon Plantation offers tours of this historical site.
Painted Sky Alpaca Farm & Fiber Mill
95 Knight House LnThere is not a kayak rental place really close to the house unfortunately. I know this place rents them in North East, MD and potentially would even deliver them. I have never used them so don’t know exactly how it works. If you do use them, let me know what you think!
7 locals recommend
Bay Venture Outfitters
West Church Point RoadThere is not a kayak rental place really close to the house unfortunately. I know this place rents them in North East, MD and potentially would even deliver them. I have never used them so don’t know exactly how it works. If you do use them, let me know what you think!