Directions from Baltimore, Maryland to Chestertown, Maryland





UpTake Roadtrip Beta

We've selected a few points along the way for you to stop. We are trying to surface things you may not find elsewhere, but if we make some poor choices, please understand. Your feedback is appreciated.


Gwynns Falls Valley From Work to Play

Landmarks – Baltimore, Maryland

Inscription. As the Baltimore and Frederick-Town Turnpike twisted and turned westward, it passed one of the centers of early city industry. A three mile long millrace on the Gwynns Falls provided power for over twenty mills that sawed ... More on HMDB

Waterfront Warehouse

Things To Do – Annapolis, Maryland

Visit a rare surviving example of the small warehouses that dotted the Annapolis waterfront in the 18th and early 19th centuries. See ... More on VisitAnnapolis.org

Belvoir (Scotts Plantation)

Landmarks – Crownsville, Maryland

Inscription. French troops under Count de Rochambeau made their 36th camp here September 16-17, 1781, enroute to Yorktown, Virginia. Most of the troops embarked from Annapolis, but the artillary marched to Georgetown to cross the ... More on HMDB

Roosevelt Park / Roosevelt Park Recreation Center

Parks – Baltimore, Maryland

about Roosevelt Park / Roosevelt Park Recreation Center: Roosevelt Park is home to the Roosevelt Park Recreation Center, playing fields, a large outdoor pool and separate kiddie pool with fountains, and playgrounds, and is planned ... More on GoCityKids

Four Rivers: The Heritage Area of Annapolis, London Town & South County

Things To Do – Annapolis, Maryland

The mission of Four Rivers is to protect and strengthen the natural, historic and cultural resources of the heritage area; to nurture their discovery through educational and ... More on VisitAnnapolis.org

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  • Four Rivers connects visitors and residents with local heritage through development and support of tourism products, such as brochures, exhibits, ... More on Discover America

The Hays House Built 1788

Landmarks – Bel Air, Maryland

Inscription. One of the earliest buildings in Bel Air. Enlarged in 1814 by Thomas A. Hays (1780–1861), an attorney, landowner and entrepreneur. Moved to present location in 1960. Retains original interior features and woodwork, ... More on HMDB

Gilpin's Falls Covered Bridge

Things To Do – North East, Maryland

View from Rt. 272; 119-ft. red wooden bridge built circa 1860. Recent restorations have helped maintain its beauty. More on Search.visitmaryland.org

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  • Inscription. Built circa 1860, the bridge is one of the few covered ones left in Maryland and the only one on public ground in Cecil County. The area to the East has been the site of several mills,... More on HMDB

Count de Rochambeaus Troops

Landmarks – Perryville, Maryland

Inscription. Crossed the Susquehanna River in five divisions and made their 23rd camp here at the end of August 1782 on the return from Yorktown victory to the north. , Erected by Maryland Historical Trust & Maryland State Highway ... More on HMDB

Chuck E Cheese

Things To Do – Highlandtown, Maryland

We also provide great food for the family including freshly baked pizzas and a garden fresh salad bar. We are a great place to take the kids for everyday fun or for special occasions such as birthdays, play groups and school fundraising ... More on familydaysoutusa

Exscape Niteclub

Things To Do – Middle River, Maryland

Exscape Niteclub - Happy hour never looked so good. Exscape Niteclub, located at 10025 Pulaski Hwy caters to an anxious after-work ... More on clubzone

Greenbacks Bar & Grill

Restaurants – Baltimore, Maryland

Kirby & Holloway Family Restaurant

Restaurants – Dover, Delaware

There is a reason for that-it's a great value and features very good local, Eastern Shore cuisine at grea... More on TripAdvisor

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  • All and all a great find I highly recommend. More on Yahoo! Travel

  • We first stopped at Kirby-Halloway Family Restaurant on a long drive from Connecticut to North Carolina, ju... More on igougo

Drifters Raw Bar & Grill

Restaurants – Baltimore, Maryland

This upscale bar and restaurant called Drifters has been serving Federal Hill's many young urban professionals since the mid-1980s. The food tends mainly toward sandwiches salads and other comfort foods but all are prepared with a ... More on Yahoo! Travel