Maryland is packed with surprises, and this road trip proves you don’t need to cross an ocean to find castle towers, grand stone architecture, and beautiful vineyards that look straight out of a storybook.
Along the way, you’ll discover historic landmarks with fascinating pasts, and scenic wineries surrounded by rolling rows of grapevines.
One stop features eye-catching castle-inspired design, while another pairs award-winning wines with sweeping countryside views and acres of picturesque farmland.
If you’re looking for a day trip filled with beautiful scenery, local wine, unique history, and plenty of photo-worthy stops, this magical Maryland adventure deserves a spot at the top of your travel list.
1. Moorish Tower (Baltimore)
The Moorish Tower stands in Baltimore’s Druid Hill Park beside Druid Lake, and this eye-catching landmark was designed by architect George A. Frederick in 1870 with arched windows and striking Moorish Revival details.
Known as one of Baltimore’s most unusual historic structures, the tower originally served as an observation tower for visitors and was built as a decorative park feature overlooking the reservoir.
As you explore the park, you can admire the tower’s distinctive design, photograph its intricate architecture, and enjoy views of the surrounding lake, walking paths, and one of Baltimore’s oldest public green spaces.
2. Linganore Winecellars (Mount Airy)
Next, head to Linganore Winecellars in Mount Airy, a family-owned winery that has been producing Maryland wines since 1976 on a scenic property surrounded by rolling vineyards.
The winery is best known for its award-winning selections, including the popular Dry Rose wine, and its tasting room lets you sample a wide range of reds, whites, fruit wines, and seasonal specialties.
You can stroll past rows of grapevines, relax on the outdoor grounds, and visit during major events hosted throughout the year.
With more than 30 wines produced on-site, live music weekends, and sweeping vineyard views of Frederick County, there are plenty of reasons to include this on your road trip.
3. Big Cork Vineyards (Rohrersville)
From Mount Airy, continue west to Big Cork Vineyards in Rohrersville, where 100 acres of vineyards stretch across the countryside with beautiful views of South Mountain and the surrounding farmland of Washington County.
Founded in 2011 by vintners Randy Thompson and David Collins, this winery has earned a reputation for producing highly rated wines, including Cabernet Franc, Viognier, and Petit Verdot, using grapes grown on the estate.
The tasting room features massive windows that frame the vineyard-covered hills, and the spacious outdoor patio is a great place to sip a glass while taking in the scenery.
You can enjoy guided tastings, seasonal events, and live music performances, making Big Cork Vineyards a lively stop where award-winning wines and some of Maryland’s most impressive vineyard views come together in one unforgettable setting.
4. The Castle At Forest Glen (Silver Spring)
Leaving the vineyard-covered hills behind, make your way to Silver Spring to see The Castle at Forest Glen, one of Maryland’s most surprising landmarks and a building that looks like it belongs in a European storybook.
This striking structure was completed in the late 1800s as part of a grand resort hotel and features towers, battlements, and turrets inspired by European castles.
Although the castle is not open for public tours and functions as a private commercial building, you can still admire its dramatic architecture from outside.
5. Old Gate of Henderson Castle (Washington, D.C.)
After spotting a full-scale castle in Silver Spring, continue into Washington, D.C., to find the Old Gate of Henderson Castle, a fascinating remnant of one of the capital’s grandest Gilded Age estates.
The stone gate once marked the entrance to Henderson Castle, the enormous residence built by U.S. Senator John B. Henderson, the Missouri politician best known for introducing the 13th Amendment that abolished slavery.
Today, the gate stands as a rare piece of the long-gone estate, giving you a glimpse into a time when sprawling mansions occupied the hills above the city instead of modern neighborhoods and busy streets.
While the castle itself no longer exists, the weathered stonework of the old gate and its historic significance make it worth seeing.
6. Robin Hill Farm & Vineyards (Brandywine)
From a hidden piece of Washington history, the road trip swings back into Maryland wine country at Robin Hill Farm & Vineyards in Brandywine, a family-owned winery set on a picturesque farm in Prince George’s County.
The vineyard is known for producing small-batch wines from estate-grown grapes, with varieties such as Chambourcin, Vidal Blanc, and Chenin Blanc thriving in the region’s climate.
You can relax in the welcoming tasting room, sip wine on the outdoor patio overlooking the vines, or visit during special events that often feature live music, local food vendors, and seasonal celebrations.
Surrounded by open fields and neatly planted vineyard rows, Robin Hill Farm & Vineyards offers a peaceful change of pace and a chance to enjoy handcrafted Maryland wines in a beautiful countryside setting, roughly a 50-minute drive from the nation’s capital.
7. Running Hare Vineyard (Prince Frederick)
As the journey heads toward the Chesapeake Bay region, make a stop at Running Hare Vineyard in Prince Frederick, a 300-acre property that combines award-winning wines with one of the most impressive winery settings in Southern Maryland.
The vineyard produces a wide selection of wines, including Cabernet Franc, Chardonnay, and Vidal Blanc, and its spacious tasting room makes it easy to sample several local favorites in one visit.
One of the standout features is the beautifully landscaped grounds, complete with colorful gardens, walking paths, and a distinctive Tuscan-inspired villa that gives the property a unique look.
You can enjoy live concerts, relax with vineyard views, and soak up the scenery, making Running Hare Vineyard the perfect finale to this road trip.
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