Overview
Leonardtown is a city in Southern Maryland.
2 things to do · 1 places to eat · 2 bars & cafés · 1 places to stay
Updated from Wikivoyage on 1 October 2026 · Something wrong or missing? Improve it on Wikivoyage
Best things about Leonardtown
Hillside Ride
Hillside Ride at Breton Bay is a premier, full valet with shuttle service, mobile advertisement company that uses Neighborhood Electric Vehicles (NEVs)
Port of Leonardtown Public Park
A little known, secret hidden along the McIntosh Run in Leonardtown is the Port of Leonardtown Public Park. This developing passive park and winery is the launch point of a nearly 3-mile, serene canoe/kayak trail. As you…
Plan your trip
Best time to visit & weather
Most comfortable: Apr–Oct. Summer highs reach about 90°F; winter lows dip to about 30°F. Very hot (Jul) — plan outdoor time for mornings. Wettest: Jul and Jun. (climate data from nearby Washington, D.C.)
Blue bars: average daily high and low (°F). Purple columns: average monthly rain and melted snow (inches).
Getting there
- From you: to see whether to drive or fly, and how long it takes.
- DCA Ronald Reagan Washington National Airport, Washington — 44 mi away (major hub). Directions
- SBY Salisbury Ocean City Wicomico Regional Airport, Salisbury — 61 mi away. Directions
Leonardtown is on Route 5 about 1.5 hours from Annapolis and 1 hour from Washington D.C. The Southern Maryland express can take visitors between the area and major airports nearby.
Full “Get in” guide ↓Budget & where to stay
No prices are listed for this place yet. See the Sleep guide ↓ for options.
Sample 1-day itinerary
Day 1
- Morning Hillside Ride
- Lunch The Slice House
- Afternoon Port of Leonardtown Public Park
- Evening Port of Leonardtown Winery
Stops are grouped by area so each day needs little backtracking. Check opening hours before you go.
Food for you
Cuisine (tap to filter)
What to ask about, for your diet
Diet labels come from each listing's description and cuisine; “likely” means the cuisine usually has good choices, not a promise. Check with the restaurant. Open the food finder
Photos
Get in
By car
Leonardtown is on Route 5 about 1.5 hours from Annapolis and 1 hour from Washington D.C. The Southern Maryland express can take visitors between the area and major airports nearby.
Get around
Do Hillside Ride
Hillside Ride at Breton Bay is a premier, full valet with shuttle service, mobile advertisement company that uses Neighborhood Electric Vehicles (NEVs)
See
Leonardtown has a vibrant arts and entertainment district, home to a music school, art galleries, a chocolatier, a painting studio, and shops for antiques and flowers.
Do
Do Port of Leonardtown Public Park
A little known, secret hidden along the McIntosh Run in Leonardtown is the Port of Leonardtown Public Park. This developing passive park and winery is the launch point of a nearly 3-mile, serene canoe/kayak trail. As you paddle along the McIntosh Run you will pass through a 58-acre Forest Interior Dwelling Species Habitat. This area is home to bald eagle families, Baltimore Orioles, wild turkeys and many other bird species. The trail terminates at the Leonardtown Wharf Public Park. Bring a picnic lunch or stroll up to Leonardtown Square and enjoy lunch at a restaurant.
Buy
The local Amish communities have auctions where they sell crafts like quilts.
Eat
Eat The Slice House
Pizza restaurant.
Drink
Drink Port of Leonardtown Winery
A cooperative winery that sources its grapes from a dozen vineyards in Southern and Eastern Maryland.
Sleep
Stay Executive Inn & Suite Park Avenue Hotel
Fitness center, sauna, bar & cafe/lounge, continental breakfast, business center, 100% non-smoking.
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My experience
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