The House on the Hill Guidebook
Food scene
On top of having a fantastic menu, great food and a short walk away from the house, this restaurant has fantastic ambience and is run by the homeless shelter, so the staff is incredibly helpful, motivated and progressive.
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Light House Bistro
202 West StOn top of having a fantastic menu, great food and a short walk away from the house, this restaurant has fantastic ambience and is run by the homeless shelter, so the staff is incredibly helpful, motivated and progressive.
The line can be long, but that's a testament to the popularity of this breakfast place. Very allergy-friendly, insanely great food and it's about a 60-second walk from my front door.
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Miss Shirley's Cafe, Annapolis
1 Park PlThe line can be long, but that's a testament to the popularity of this breakfast place. Very allergy-friendly, insanely great food and it's about a 60-second walk from my front door.
Definitely my favorite place to go with a group of people or solo. They have a ton of options so everyone can find what they want and sit together inside or outside. Sometimes there's live music and there are board games to play.
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Market House
25 Market SpaceDefinitely my favorite place to go with a group of people or solo. They have a ton of options so everyone can find what they want and sit together inside or outside. Sometimes there's live music and there are board games to play.
Want to go where all of the local sailors go? Head to the Boatyard Bar & Grill for exquisite food, the best crab cakes in town and an upbeat vibe.
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Boatyard Bar & Grill
400 Fourth StWant to go where all of the local sailors go? Head to the Boatyard Bar & Grill for exquisite food, the best crab cakes in town and an upbeat vibe.
Vin 909 Winecafe
909 Bay Ridge AveAmazing local and seasonal food with a huge wine selection
Neighborhoods
The perfect place to walk, dine, sight-see and be near the water. There's history everywhere around you.
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Main Street
Main StreetThe perfect place to walk, dine, sight-see and be near the water. There's history everywhere around you.
The Spa Creek bridge will take you over to Eastport, a historic neighborhood on a peninsula filled with beautiful homes, restaurants and a ton of marinas.
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Eastport
The Spa Creek bridge will take you over to Eastport, a historic neighborhood on a peninsula filled with beautiful homes, restaurants and a ton of marinas.
Sightseeing
Want to get on the water? The Schooner Woodwinds were featured in the movie "Wedding Crashers" and are a gorgeous and comfortable adventure.
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Schooner Woodwind Sailing Cruises
80 Compromise StWant to get on the water? The Schooner Woodwinds were featured in the movie "Wedding Crashers" and are a gorgeous and comfortable adventure.
Parks
A very beautiful and extensive park not too far away, which is great for ice skating in the winter time or bike riding, walking, picnicking and throwing a frisbee in the warmer months.
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Quiet Waters Park
600 Quiet Waters Park RdA very beautiful and extensive park not too far away, which is great for ice skating in the winter time or bike riding, walking, picnicking and throwing a frisbee in the warmer months.
Winery
Just a few minutes drive away, you're in the country, in a restored barn, on a vineyard, sipping wine.
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Great Frogs Winery
3218 Harness Creek RdJust a few minutes drive away, you're in the country, in a restored barn, on a vineyard, sipping wine.
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Ukuzulazula
Water Taxi
There's a water taxi that can give you a tour of Annapolis from the water and/or a pick up drop off to different locations around Annapolis and Eastport. Common places to pick it up are on the right side of Ego Alley about half way down and the Chart House in Eastport. It will pick you up and drop you off anywhere you want though for a few dollars.
Ukuzulazula
Circulator Shuttle
If you see a shuttle with "Circulator" written on the side of it, flag it down and hop on for free. It drives along the main roads of Annapolis.
Ungaphuthelwa
First Sunday Arts Festival
We invite you to visit the festivals and shop over 130 artists on the first Sunday of each month May through November in downtown Annapolis Maryland from 11am to 5pm except November which is 11am to 4pm.
Ungaphuthelwa
Dinner Under the Stars
Every Wednesday and Saturday evening in the warmer months, the farthest east block of West Street is blocked off to cars and the restaurants set up in the street. There's live music, dancing, ping pong and even pickle ball!
Ungaphuthelwa
Wednesday Night Racing (sailing)
May-August, almost 150 sailboats race on Wednesday nights. They start out in the Severn River and the most epic part- they all finish right by the Eastport Bridge! Hop up there between about 7:15pm and 8pm for a grand spectacle or book a ride on the Schooner Woodwinds to be a part of the race yourself.