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Voykit pocket guide · United States
Leonardtown
Give Leonardtown one night, or a half-day stop between Point Lookout and St. Mary's City: the square, the wharf and the winery fill an afternoon.
Leonardtown is the seat of St. Mary's County, a small town on Breton Bay about 1 h 30 min by car from Annapolis and roughly 1 h from Washington, DC. Its draw is a compact historic square with galleries and shops, a wharf park on the water, a cooperative winery and a paddling trail on the McIntosh Run. It works as a base for Southern Maryland's colonial sites, not as a destination on its own.
- Country
- United States
- Best months
- Apr–Jun, Sep–Oct
- Avoid
- Jul–Aug (heat and humidity)
- Stay
- 1 night
Checked 2026-09. Prices, hours and rules change; anything marked (check) is not confirmed.
Essentials
- Currency
- USD
- Money
- Currency is the US dollar (USD, $). Cards and phone payments work almost everywhere; carry a little cash for tips and small vendors.
- Daily spend
- Budget $70–110 excl. bed · Mid $120–190 excl. bed · High $200+ excl. bed (estimate; check)
- SIM and data
- AT&T, Verizon and T-Mobile cover the country; prepaid SIMs at their stores and Walmart/Target (passport required), or an eSIM before you fly.
- Emergency
- Police, fire, ambulance 911
- Plugs
- Types A, B · 120 V · 60 Hz · Chargers are dual-voltage; hair dryers and straighteners from 230 V countries need a converter.
- Tipping
- Sit-down restaurant: 18–22% of the pre-tax bill.; Bar: US$1–2 per drink or 20% of the tab.; Taxi / ride-hailing: 15–20%, in the app.; Hotel housekeeping: US$3–5 a night.; Porter / valet: US$2–5 per bag or car.; Tour guide: US$10–20 per person for a day tour.; Counter service / tablet prompts: Optional; 0–15%.
- Water
- Tap water is drinkable nearly everywhere; boil or treat water from streams in parks.
- Toilets
- Free public toilets are scarce in big cities; use cafés, department stores, libraries, stations. Rest areas on highways are free.
What things cost
| Item | Price |
|---|---|
| Coffee | $3–5 |
| Deli sandwich or crab cake | $10–20 |
| Pizza, one large | $18–26 |
| Winery tasting | $10–15 |
| Canoe or kayak rental on the McIntosh Run | $30–50 |
| Gallon of fuel | $3.20–3.80 |
Desk estimates, checked 2026-09; check locally.
Get in
By air
- DCA · Ronald Reagan Washington National
- About 1 h 30 min by car via Route 5; the closest big-hub airport.
- BWI · Baltimore/Washington International
- About 1 h 45 min by car; more low-cost flights.
- IAD · Washington Dulles International
- About 2 h by car; long-haul international arrivals.
Typical fares
- DCA → Leonardtown by car
- about 1 h 30 min, roughly 90 km (56 mi)about 1 h 30 min, roughly 56 mi (90 km)
- Rental car, one day
- $50–80 plus fuel
- Winery tasting
- $10–15
Show 7 more sections and the pocket cardHideGet around, See and do, Sleep, Phrase card, Etiquette, safety and scams, One and two days, Sources, Pocket card
Get around
A car is close to essential: sights sit along Route 5 and the bay roads, and there is no useful local bus. The square, wharf and market are walkable from each other in 10–15 min. Parking in the historic district is free but tight on event weekends.
See and do
Known for
- Historic Leonardtown Square
- Port of Leonardtown Winery
- Leonardtown Wharf and the McIntosh Run paddling trail
- Shepard's Old Field Market
Day trips
| Where | How | Time |
|---|---|---|
| St. Mary's City | Drive Route 5 south, about 15 min | About 20 min |
| Point Lookout | Drive Route 5 south through Lexington Park, about 40 min | About 45 min |
| Solomons | Drive Route 5 north to Route 4, then east across the Patuxent River bridge, about 40 min | About 45 min |
| Lexington Park | Drive Route 235 south, about 20 min | About 25 min |
| Chesapeake Beach | Drive Route 4 north, about 1 h | About 1 h 10 min |
| Cobb Island | Drive Route 257 south, about 45 min | About 50 min |
Sleep
- Leonardtown Square and Washington Street
- Walk to restaurants, galleries and the market; the only place where you can leave the car parked.
- Route 5 strip (north of town)
- Chain motels and free parking; 5–10 min drive to the square, no walkable food.
- Lexington Park / California, MD
- More beds and services 20–25 min south, near the Patuxent River naval base; use it if Leonardtown is full.
Phrase card
| English | Say or show |
|---|---|
| Where is the square? | Where is the square? |
| Can I pay by card? | Can I pay by card? |
| Is the kitchen still open? | Is the kitchen still open? |
| One night, two people | One night, two people |
Etiquette, safety and scams
Etiquette
- Greeting: Handshake and 'hi, how are you?' — reply 'good, thanks'; avoid: Treating the question as a real health enquiry
- Restaurants: Tip 18–22% and wait for the check; avoid: Leaving without tipping
- Personal space: Keep an arm's length in queues; avoid: Standing close to strangers
- Politics and religion: Listen more than you speak; avoid: Opening with hot-button topics
- Smoking: Smoke only in marked areas; avoid: Smoking near doors or in parks where banned
Scams and watch-outs
- Distances look short on the map but Route 5 is a two-lane road with traffic: allow more time than the mileage suggests.
- Many kitchens close by 21:00 and some places shut Sunday–Monday; check hours before you drive out.
- Summer heat and humidity on the water; ticks and poison ivy on the paddling-trail banks.
- Cell signal is patchy on the bay-side back roads.
A quiet small town; the real risks are driving Route 5 at night, deer on the road, and summer heat on the water. Violent crime is rare, but lock the car and don't leave valuables visible at trailheads.
One and two days
No timed day plan for Leonardtown yet. Suggested stay: 1 night. Build a day from the list below, mornings for the big sight.
- Historic Leonardtown Square
- Port of Leonardtown Winery
- Leonardtown Wharf and the McIntosh Run paddling trail
- Shepard's Old Field Market
Sources
Written by Voykit; facts cross-checked against these sources, last desk check 2026-09. Prices, hours and rules change: check on the day.
- Shepard's Old Field Market: www.shepherdsoldfield.com/
- Wikivoyage: Leonardtown, revision 5242669 (CC BY-SA 4.0): en.wikivoyage.org/w/index.php?oldid=5242669
Pocket card
Cut along the border and keep it in your wallet. Show the local-script lines to a driver.
Leonardtown
To this address, please
To this address, please
My hotel (write the name and address in the local script)
- Police, fire, ambulance911
No embassies here; the nearest consulates are in Washington, DC, about 1 h 30 min away.
Tipping is expected: 18–22% at sit-down restaurants, $1–2 a drink, 15–20% taxis.
Voykit · checked 2026-09
Printed from Voykit (/leonardtown). Written by Voykit; checked 2026-09. Estimates only: confirm prices, hours and entry rules on the day.