5 days in Leonardtown Itinerary

Created using Inspirock Leonardtown travel planner
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Make it your trip
+2
Drive to Chicago Midway International Airport, Fly to Ronald Reagan Washington National Airport, Drive to Leonardtown
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Leonardtown
— 4 nights
+2
Drive to Ronald Reagan Washington National Airport, Fly to Chicago Midway International Airport, Drive to Bolingbrook

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Leonardtown — 4 nights

Leonardtown is a town in and the county seat of St. Venture out of the city with trips to Stratford Hall (in Stratford), Reedville Fishermen's Museum (in Reedville) and Governor Harry W. Nice Memorial Bridge (in Newburg). There's lots more to do: learn about winemaking at Port of Leonardtown Winery, immerse yourself in nature at Calvert Cliffs State Park, stroll around Leonardtown Wharf Park, and visit a coastal fixture at Calvert Marine Museum and Drum Point Lighthouse.

For where to stay, other places to visit, reviews, and other tourist information, you can read our Leonardtown tour builder website.

Bolingbrook to Leonardtown is an approximately 6-hour combination of car and flight. You can also drive. The time zone changes from Central Standard Time to Eastern Standard Time, which is usually a 1 hour difference. Traveling from Bolingbrook in November, things will get somewhat warmer in Leonardtown: highs are around 57°F and lows about 38°F. Wrap up your sightseeing on the 26th (Sat) early enough to drive back home.
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Museums · Historic Sites · Wineries · Parks
Side Trips