Need a Weekend to Slow Down? Take the Scenic Route Through Maryland

Sometimes doing less is the best way to experience more.

Have a glass of wine while overlooking the rolling hills of the scenic countryside. Make an impromptu stop at a local brewery that catches your eye. Wander through a farm market without checking the time. Take the scenic route simply because you don’t have to be anywhere at a particular time.

The best weekends don’t happen when every hour is planned. They happen when one stop naturally leads to the next, when a quick tasting turns into an afternoon well spent, or when you decide to pull over simply because the view deserves it.

That’s the spirit behind Montgomery County, Maryland‘s Tastemaker’s Trail. Through the self-guided collection of wineries, breweries, distilleries, and other craft beverage destinations you can weave through the area with loose plans and choose your own adventure.

Here’s how to get started.

Friday: Leave the Rush Behind

By the time you cross into Montgomery County, you’ve already accomplished the hardest part of the weekend: leaving work behind.

Check into the Gaithersburg Marriott Washingtonian Center for a central location with everything you need just steps away. Drop your bags and stretch your legs with a walk around Rio, a waterfront destination featuring lakeside dining, boutique shopping, and concerts throughout the summer. Settle in for a relaxing dinner, grab something quick, or unwind at the hotel’s restaurant, The Bench, with a signature burger featuring a juicy beef patty, bacon, American cheese, and house burger sauce before heading to bed.

Saturday: Sip, Savor, Repeat

Start your morning with a signature iced hazelnut latte from Tous Les Jours, a specialty Korean French bakery café at Rio, then venture out for a morning hike along the wooded trails of Sugarloaf Mountain. The higher you climb, the more the surrounding countryside unfolds below, rewarding you with sweeping views across Montgomery County’s rolling landscape. 

After descending, lunch is the next stop. Pause for a memorable farm-inspired meal at The Comus Inn, where a Maryland crab dip appetizer and signature Inn Smash Burger pair perfectly with views of Sugarloaf Mountain.

Continue your afternoon along the Tastemakers Trail to discover more of Montgomery County’s craft beverage and farm-to-table food scene at your own pace. Some stops are tucked into the countryside, while others are found in busy downtown areas, making it easy to customize where you stop based on what you’re in the mood for. 

Make an afternoon of it at Sugarloaf Mountain Vineyard, where the landscape you’ve just admired becomes part of the tasting experience. Award-winning wines, live music, and expansive outdoor seating encourage visitors to slow down and settle in for a while.

One standout spot is Song Dog Farm Distillery, where founders Megan Draheim and David Harris drew on their backgrounds in conservation to create a distillery that celebrates sustainable agriculture alongside handcrafted spirits. Another local favorite on the trail is Windridge Vineyards, , a family-owned farm with estate wines, generous charcuterie boards layered with savory cured meats, and rolling hillside views that invite a perfectly unhurried afternoon.

Take a break between tastings at Button Farm Living History Center, where hands-on demonstrations and a preserved working farm offer a glimpse into Montgomery County’s rich agricultural heritage. Discover the land, traditions, and people who have shaped the regions’ farming legacy for generations.

Sunday: One Last Stop (or Two)

Before heading back toward Philly, spend your final morning exploring the stories that have shaped not just Montgomery County, but the nation itself.

Start with brunch at Zinnia in Silver Spring, where seasonal dishes are served inside a beautifully restored 19th-century home surrounded by lush gardens. It’s the kind of place that invites you to slow down one last time before hitting the road.

From there, make your way to Historic Brookeville, the small town that famously served as the nation’s capital for a day during the War of 1812. Its preserved buildings and quiet streets offer a glimpse into a chapter of American history that many travelers didn’t know existed.

Before heading home, make one final stop at Lone Oak Farm Brewing Co. and Fallen Oak Distilling, not for another tasting, but for the story. The family-owned destination was built around a towering oak tree that stood on the property for more than 250 years. When the tree fell in 2023, its wood was repurposed throughout the property, including the fireplace mantle inside the Fallen Oak’s speakeasy, preserving a piece of the farm’s history for future visitors. It’s a fitting reminder that the Tastemakers Trail isn’t just about what’s in your glass; it’s about the people, traditions, and sense of place behind every stop.

Plan to head back to Philadelphia by early afternoon to stay ahead of weekend traffic. By then, you’ll already be planning which stop to revisit first.

Ready to map out your own getaway? Visit visitmontgomery.com for more itinerary inspiration, explore additional stops along the Tastemakers Trail, and discover places to stay. 

This is a paid partnership between Visit Montgomery, MD and Philadelphia Magazine