If your perfect road trip includes sipping local wine, discovering historic covered bridges, and wandering through charming small towns, this Maryland adventure belongs at the top of your list.
You’ll wind past rolling farmland, scenic mountain views, and hidden backroads that lead to places packed with history and unforgettable photo opportunities.
Along the way, you’ll find cozy cafes, unique local shops, and some of the state’s most memorable landmarks, all within an easy drive of one another.
Fill up the gas tank, and get ready for a fun road trip that blends relaxing winery stops, fascinating history, and picture perfect scenery from start to finish.
1. New Market
New Market is a small town in Frederick County that features a beautifully preserved Main Street, lined with brick buildings, antique shops, local boutiques, and historic homes dating back to the early 1800s.
The town is known as the “Antiques Capital of Maryland,” so you can spend hours browsing vintage furniture, collectibles, handmade gifts, and one of a kind finds before stopping at a cozy cafe or bakery.
After shopping, take a walk through the historic district to see old storefront details, classic porches, and quiet side streets.
Then check the town calendar for seasonal events or grab a meal and a sweet treat along Main Street.
2. Linganore Winecellars
Just a few minutes from New Market, Linganore Winecellars has been welcoming wine lovers since 1976 and is one of Maryland’s oldest family owned wineries, with 230 acres of vineyards spread across rolling Frederick County hills.
You can choose from dozens of wines, including the popular Late Harvest Vidal Blanc, Mountain Red, and Raspberry, then relax on the spacious lawn with a picnic while enjoying peaceful vineyard views.
The winery is also famous for hosting lively events like the Caribbean Wine and Music Festival and wine tasting weekends that draw crowds from across the region.
If you want to bring home a memorable souvenir, stop by the tasting room for a bottle of wine or a gift before continuing your road trip through Maryland’s scenic countryside.
3. Loy’s Station Covered Bridge
Next, take a 30-minute drive to Loy’s Station Covered Bridge, a charming wooden bridge that crosses Owens Creek near Thurmont.
Built in 1860, the bridge stretches 90 feet across the creek and was carefully reconstructed after being destroyed in 1991, preserving its historic multiple king post truss design.
You can pull over for photos, listen to the gentle sound of the water below, and admire the bright red exterior that stands out against the surrounding trees in every season.
Loy’s Station Covered Bridge also sits just a short drive from Cunningham Falls State Park and Catoctin Mountain Park, making it easy to pair this quick stop with even more scenic mountain views.
4. Roddy Road Covered Bridge
Keep the covered bridge adventure going with Roddy Road Covered Bridge, where this postcard worthy landmark has been carrying travelers across Owens Creek since 1856.
At 40 feet long, it is one of Maryland’s shortest covered bridges, but its distinctive red wooden exterior, classic King post truss design, and quiet country setting make it one of the state’s most photographed stops.
You can park nearby for a closer look, snap pictures from both sides of the creek, and enjoy the peaceful farmland and wooded scenery that surrounds the bridge.
Roddy Road Covered Bridge is listed on the National Register of Historic Places and makes a fun stop between nearby parks, wineries, and small towns.
5. Thurmont
Next, roll into Thurmont, a friendly small town in northern Frederick County that serves as the gateway to some of Maryland’s best outdoor adventures.
You can explore the colorful shops and restaurants downtown before heading a few miles to Cunningham Falls State Park, where the 78 foot cascading waterfall is the tallest in Maryland, or visit nearby Catoctin Mountain Park for scenic hiking trails.
History is part of the experience too, with the Catoctin Furnace Historic Site showcasing one of the nation’s earliest ironmaking communities.
Thurmont also hosts popular events like Colorfest each October, one of the largest arts and crafts festivals on the East Coast, drawing hundreds of vendors and thousands of visitors every year.
6. Utica Mills Covered Bridge
After exploring Thurmont, take a scenic drive to Utica Mills Covered Bridge, a quiet historic crossing over Fishing Creek that has been part of the countryside since 1891.
The 101-foot long bridge features a classic Burr arch truss design and is one of Maryland’s few remaining authentic covered bridges.
You can walk across the wooden bridge, listen to the creek flowing below, and enjoy the peaceful farmland, towering trees, and winding backroads that surround the area.
Utica Mills Covered Bridge sits close to the tiny community of Utica and makes an easy stop as you continue toward more beautiful stretches of Maryland’s rolling countryside.
7. Middletown
Continue driving just 20 minutes to Middletown, a charming town in the heart of the Middletown Valley, where historic streets and beautiful mountain views make it a rewarding road trip stop.
You can stroll along Main Street to browse independent shops, grab fresh pastries or coffee from local favorites, and admire well preserved 19th century buildings that reflect the town’s long history.
Just outside town, don’t miss South Mountain Creamery, where you can meet farm animals, enjoy homemade ice cream, and pick up fresh milk, cheese, and other local products straight from the farm.
If you have extra time, drive a few minutes to Washington Monument State Park, home to the nation’s first completed monument honoring George Washington, along with hiking trails and sweeping views across the Cumberland Valley.
8. Big Cork Vineyards
Wrap up your road trip at Big Cork Vineyards in Rohrersville, where more than 40 acres of estate vineyards stretch beneath the slopes of South Mountain, creating one of the most scenic winery settings in Maryland.
The award winning winery is known for producing Cabernet Franc, Petit Verdot and Chardonnay, plus you can enjoy guided tastings inside the modern tasting room or on the spacious outdoor patio.
Live music, food trucks, and seasonal events fill the calendar throughout the year, making it easy to linger a little longer while soaking in the sweeping vineyard and mountain views.
Before you hit the road, browse the winery shop for a bottle to take home, then raise one final glass to a trip filled with historic covered bridges, welcoming small towns, and unforgettable Maryland wine country.
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