Port of Leonardtown Winery (Leonardtown, Maryland)
Leonardtown, Maryland, a charming and historic town, is home to the renowned Port of Leonardtown Winery. Known for its vibrant community and picturesque landscapes, Leonardtown offers a delightful blend of history and modern attractions. Visitors can explore the beautiful town square, historic buildings, and enjoy waterfront views at Leonardtown Wharf Park. CliftonCab services cater to the unique needs of both residents and tourists, ensuring convenient, safe, and comfortable transportation. Whether you’re heading to a wine tasting at the Port of Leonardtown Winery or exploring local shops and eateries, CliftonCab guarantees a seamless travel experience tailored to your itinerary.
Restaurants near Port of Leonardtown Winery
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The Front Porch
American
22770 Washington St, Leonardtown, MD 20650
(301) 997-1009
Located in a historic building, The Front Porch offers classic American cuisine with a modern twist, featuring locally sourced ingredients and seasonal dishes. Guests can enjoy a cozy, inviting atmosphere with exceptional service.

Monday
Closed
Tuesday
11:00 AM – 9:00 PM
Wednesday
11:00 AM – 9:00 PM
Thursday
11:00 AM – 9:00 PM
Friday
11:00 AM – 10:00 PM
Saturday
11:00 AM – 10:00 PM
Sunday
10:00 AM – 8:00 PM
Olde Town Pub
Pub
22785 Washington St, Leonardtown, MD 20650
(301) 475-8184
A cozy, local favorite offering a wide selection of craft beers, delicious pub fare, and a friendly atmosphere. It’s the perfect spot for a casual night out with friends or family.

Monday
11:00 AM – 9:00 PM
Tuesday
11:00 AM – 9:00 PM
Wednesday
11:00 AM – 9:00 PM
Thursday
11:00 AM – 9:00 PM
Friday
11:00 AM – 10:00 PM
Saturday
11:00 AM – 10:00 PM
Sunday
11:00 AM – 8:00 PM
Kevin’s Corner Kafe
American
24509 Point Lookout Rd, Leonardtown, MD 20650
(301) 997-1260
Known for its hearty breakfasts and homestyle cooking, Kevin’s Corner Kafe is a beloved local spot. The friendly service and comforting dishes make it a must-visit.

Monday
6:00 AM – 2:00 PM
Tuesday
6:00 AM – 2:00 PM
Wednesday
6:00 AM – 2:00 PM
Thursday
6:00 AM – 2:00 PM
Friday
6:00 AM – 2:00 PM
Saturday
6:00 AM – 2:00 PM
Sunday
7:00 AM – 2:00 PM
The Rex
American
22695 Washington St, Leonardtown, MD 20650
(301) 475-1512
Offering a contemporary dining experience with a menu that includes seafood, steaks, and vegetarian options, The Rex is perfect for both casual meals and special occasions.

Monday
11:00 AM – 9:00 PM
Tuesday
11:00 AM – 9:00 PM
Wednesday
11:00 AM – 9:00 PM
Thursday
11:00 AM – 9:00 PM
Friday
11:00 AM – 10:00 PM
Saturday
11:00 AM – 10:00 PM
Sunday
10:00 AM – 8:00 PM
The Slice House
Pizzeria
41565 Park Ave, Leonardtown, MD 20650
(301) 997-6597
This pizzeria offers a variety of delicious pizzas, sandwiches, and salads. The relaxed atmosphere and friendly service make it a great spot for a casual meal.

Monday
11:00 AM – 9:00 PM
Tuesday
11:00 AM – 9:00 PM
Wednesday
11:00 AM – 9:00 PM
Thursday
11:00 AM – 9:00 PM
Friday
11:00 AM – 9:00 PM
Saturday
11:00 AM – 9:00 PM
Sunday
11:00 AM – 9:00 PM
Salted Scoop
Ice Cream Parlor
22600 Washington St, Leonardtown, MD 20650
(301) 997-0722
A popular spot for dessert lovers, Salted Scoop offers a variety of unique and classic ice cream flavors. It’s the perfect place to cool down and enjoy a sweet treat.

Monday
12:00 PM – 9:00 PM
Tuesday
12:00 PM – 9:00 PM
Wednesday
12:00 PM – 9:00 PM
Thursday
12:00 PM – 9:00 PM
Friday
12:00 PM – 9:00 PM
Saturday
12:00 PM – 9:00 PM
Sunday
12:00 PM – 9:00 PM
Social Coffeehouse
Coffeehouse
41658 Fenwick St, Leonardtown, MD 20650
(240) 309-4085
This charming coffeehouse offers a variety of specialty coffees, teas, and pastries. It’s an ideal spot to relax, work, or catch up with friends.

Monday
7:00 AM – 7:00 PM
Tuesday
7:00 AM – 7:00 PM
Wednesday
7:00 AM – 7:00 PM
Thursday
7:00 AM – 7:00 PM
Friday
7:00 AM – 7:00 PM
Saturday
7:00 AM – 7:00 PM
Sunday
8:00 AM – 6:00 PM
Port of Leonardtown Winery
Winery
23190 Newtowne Neck Rd, Leonardtown, MD 20650
(301) 690-2192
Offering a variety of local wines, this winery provides a serene setting for wine tasting and tours. It’s a perfect destination for wine enthusiasts and those looking to relax in a picturesque environment.

Monday
Closed
Tuesday
Closed
Wednesday
Closed
Thursday
12:00 PM – 6:00 PM
Friday
12:00 PM – 6:00 PM
Saturday
12:00 PM – 6:00 PM
Sunday
12:00 PM – 6:00 PM
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Dulles Airport
Reagan Airport
Baltimore Airport
The Front Porch
Olde Town Pub
Kevin’s Corner Kafe
The Rex
The Slice House
Salted Scoop
Social Coffeehouse
Port of Leonardtown Winery
Wedding Venues near Port of Leonardtown Winery
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Woodlawn Farm
Historic Farm
16040 Woodlawn Dr, Ridge, MD 20680
(301) 872-0555
Nestled along the waterfront, Woodlawn Farm offers a historic and picturesque setting for weddings. The venue features stunning views, elegant event spaces, and charming accommodations.

Generic Pricing
$5,000 – $10,000
Capacity
Up to 200 guests
Website
www.woodlawn-farm.com
Historic St. Mary’s City
Historic Site
47414 Old State House Rd, St. Mary’s City, MD 20686
(240) 895-4990
This historic site offers a unique and scenic backdrop for weddings, with beautiful gardens and historic buildings that provide a touch of elegance and charm.

Generic Pricing
$3,000 – $7,000
Capacity
Up to 150 guests
Website
www.hsmcdigshistory.org
Sotterley Plantation
Plantation
44300 Sotterley Ln, Hollywood, MD 20636
(301) 373-2280
This historic plantation offers beautiful gardens, rustic barns, and scenic waterfront views, making it a perfect setting for a romantic and memorable wedding.

Generic Pricing
$4,000 – $9,000
Capacity
Up to 250 guests
Website
www.sotterley.org
Running Hare Vineyard
Vineyard
150 Adelina Rd, Prince Frederick, MD 20678
(410) 414-8486
This picturesque vineyard offers a stunning setting for weddings, with rolling hills, lush vineyards, and elegant event spaces. It’s perfect for a romantic and sophisticated celebration.

Generic Pricing
$6,000 – $12,000
Capacity
Up to 200 guests
Website
www.runningharevineyard.com
Bowles Farm
Farm
22880 Budds Creek Rd, Clements, MD 20624
(301) 475-2139
Bowles Farm provides a charming and rustic setting for weddings, with beautiful barns, scenic fields, and a warm, welcoming atmosphere.

Generic Pricing
$3,000 – $8,000
Capacity
Up to 200 guests
Website
www.bowlesfarms.com
Mary’s Hope on Church Cove
Waterfront Estate
17851 Clarke Rd, Dameron, MD 20628
(240) 925-3267
This elegant waterfront estate offers stunning views, beautifully landscaped grounds, and sophisticated event spaces, perfect for a luxurious and memorable wedding.

Generic Pricing
$7,000 – $15,000
Capacity
Up to 300 guests
Website
www.maryshope.com
Greenwell State Park
State Park
25420 Rosedale Manor Ln, Hollywood, MD 20636
(301) 373-9775
This state park offers a natural and serene setting for weddings, with beautiful waterfront views, lush landscapes, and rustic charm. It’s ideal for outdoor and nature-themed weddings.

Generic Pricing
$2,000 – $5,000
Capacity
Up to 150 guests
Website
www.greenwellfoundation.org
St. Mary’s College of Maryland
College Campus
47645 College Dr, St. Mary’s City, MD 20686
(240) 895-2000
The college campus offers a variety of beautiful settings for weddings, including waterfront views, historic buildings, and elegant event spaces. It’s perfect for a sophisticated and scholarly celebration.

Generic Pricing
$3,000 – $7,000
Capacity
Up to 200 guests
Website
www.smcm.edu
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Airport Taxi Transportation near Port of Leonardtown Winery
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