Directions from Pittsburgh, Pennsylvania 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.


Luxury on the Bay

Landmarks – Havre de Grace, Maryland

Inscription. Listen, and you can almost hear the jazz music and smell the roasting duck. Edward F. Piersol conceived the idea for the Bayou Hotel and was the first owner. The hotel, considered lavish for a small town was built with ... More on HMDB

Westminster Hall & Burying Ground

Things To Do – Baltimore, Maryland

Guided tours of burying ground and catacombs. Resting place of Edgar Allan Poe and prominent Maryland political ... More on Search.visitmaryland.org

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  • Inscription. When leaders of First Presbyterian Church decided to build an new church atop their 18th-century burying ground, they hoped to serve Baltimores growing west end and protect their buria... More on HMDB

Gibson Island Club

Golf Courses – Gibson Island, Maryland

A yacht club, swim club and very competitive tennis club complement the golf club. More on GolfReview

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  • Great views of the Chesapeake with yachts and gorgeous sailboats. More on GolfReview

  • The private Gibson Island Club is located on Gibson Island at the mouth of the Magothy River and the Chesapeake Bay. Gibson Island is midway between Annapolis and Baltimore. Access to the island is... More on GolfReview

Cobbs Brigade McLaws Division C.S.A. Lt. Col. Jefferson M. Lamar & Cobbs Georgia Legion

Landmarks – Burkittsville, Maryland

Inscription. Cobbs Brigade, McLaws Division C. S. A. —— —— At 1 P. M. on September 14, 1862, Cobbs Brigade under Gen. Howell Cobb of Athens, GA. marched from Sandy Hook to Brownsville at the west foot of South ... More on HMDB

Dr. Lamar's Sanitarium

Museums – Middletown, Maryland

Explore Dr. Lamar's Sanitarium and see his original operating room, equipment, books and medicines dating back to the early 1900's. Civil War memorabilia is on display and the public ... More on MuseumsUSA.org

Elkridge Hunt Club & Golf Course

Golf Courses – Baltimore, Maryland

Elkridge is exclusive, and you won't get to play there without being invited. But don't feel left out. The course is short, quirky and cramped. The bad and ugly holes outnumber the few good ones. ... More on GolfReview

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  • Elkridge Hunt Club is an 18-hole regulation length golf course in Baltimore, Maryland. This short layout has 3 sets of teeboxes for a fun, but challenging golfing experience. Online tee times may b... More on TheGolfCourses.net

  • This season commemorates the centennial of this well-maintained and prestigious course. The course was redesigned by Robert ... More on Golf.com

National Lacrosse Hall of Fame

Museums – Baltimore, Maryland

This was a great experience for our family. Not as big as we expected, but was still exciting for our boys who play the game. More on TripAdvisor

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  • This museum highlights 350 years of lacrosse history with rare photographs and art, vintage equipment and uniforms, striking ... More on Baltimore.org

  • This museum highlights 350 years of lacrosse history with rare photographs and art, vintage equipment and uniforms, striking ... More on Baltimore.org

Annapolis Chamber Players

Nightlife – Annapolis, Maryland

Annapolis Chamber Players is a professional mixed chamber music ensemble featuring classical favorites and lesser-known gems. This charitable organization produces ... More on VisitAnnapolis.org

Catonsville - Townsend House & Pullen Museum

Museums – Catonsville, Maryland

The Townsend House The Townsend House was the home of the late Mr. and Mrs. Robert Townsend. The house, which was designed with an eighteenth century floor plan, contains six rooms and an entry hal... More on Catonsvillehistory.org

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  • The Townsend House houses a variety of antiques from the eighteenth and nineteenth centuries as well as severa ... More on PlanetWare

Blue Star Memorial Highway

Landmarks – Somerset, Pennsylvania

Inscription. A tribute to the Armed Forces that have defended the United States of America. Following World War II, the National Council of State Garden Clubs designated certain national roads as "Blue Star Memorial Highway", as a ... More on HMDB

Life Elements Yoga and Ayurveda

Health Club – Stevensville, Maryland

All levels of instruction. Multi-disciplinary approach. Highly trained instructors, beautiful and peaceful studio. Ayurvedic ... More on YogaFinder

The Owl Bar

Restaurants – Baltimore, Maryland

The overall impression was that I have been served food and drinks in a restroom. More on CitySearch

3.5
15 reviews
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Average Rating
3.5 out of 5
15 reviews
2 sources
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4.5
5+ reviews
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  • The brick oven made the experience worthwhile. More on TripAdvisor

  • Amazingly dissatisfying place. It smells in there as in the public restroom in a big railway station. There... More on CitySearch

Bob Evans Restaurant

Restaurants – Easton, Maryland

Fairly priced homestlye food what you'd expect from any Bob Evans. More on Yahoo! Travel

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  • Excellent service by waitress Brandis! Ask for her if you passing through. Fairly priced homestlye food what ... More on Yahoo! Travel

Chiofalo's Carry Out Shop

Restaurants – Baltimore, Maryland

Good Food: I liked chiofalos pizza and cheesesteak More on Yahoo! Travel

3.5
1 source
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3.5 out of 5
overall rating
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3.5
overall rating
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  • Good Food: I liked chiofalos pizza and cheesesteak More on Yahoo! Travel