Montgomery County is Maryland’s Cultural Capital

Whether exploring the rural countryside or enjoying world-class performances and exhibits, visitors discover a destination filled with memorable moments and meaningful connections.

From scenic waterways and acclaimed museums to rolling vineyards and unique art experiences, Montgomery County, Maryland, offers group travelers a refreshing mix ofculture, cuisine, history, and relaxation just outside Washington, DC.

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Montgomery County, Maryland Day-to-Day Group Itinerary

DAY 1 of Things To Do in Montgomery County

Begin your journey at the C&O Canal National Historical Park, where history and nature come together along the banks of the Potomac River. Guests can watch the rushing rapids from the Great Falls Overlook, stroll portions of the towpath, or learn about historic canal life through ranger-led programs at the Great Falls Tavern Visitor Center.

Continue the day at Glenstone Museum, a remarkable blend of art, architecture, and nature set across 300 acres. Known for its thoughtfully curated collection of post-World WarII art, Glenstone encourages visitors to slow down and experience both the artwork and the natural environment at their own pace. Guests can also enjoy seasonal cuisine and refreshments at the museum café overlooking the grounds.

DAY 2 of Maryland Activities

Discover the scenic beauty of the rural side of Montgomery, a sprawling countryside of farms, vineyards, and breweries just beyond the city. Enjoy wine tastings and panoramic vineyard scenery at Windridge Vineyards, where rolling hills and elegant gathering spaces create the perfect setting for groups. Continue to The Comus Inn for lunch overlooking Maryland’s Sugarloaf Mountain, a longtime favorite for scenic dining, especially in the fall.

In the afternoon, experience Montgomery County’s growing craft beverage scene at Lone Oak Farm Brewing Company and neighboring Fallen Oak Distilling. Located on the same farm, the brewery offers a rustic, laid-back atmosphere while the distillery provides a more elevated tasting experience inspired by a vintage speakeasy aesthetic. Just a short drive away, groups can also explore Waredaca Brewing Company, a brewery set on a working horse farm, and Elder Pine Brewing & Blending Co., a wooded retreat where guests can relax beneath the trees while enjoying small-batch craft beer surrounded by nature.

DAY 3 of Final Montgomery Attractions

Spend the morning at The Mansion at Strathmore, home to artistic programs, rotating gallery exhibitions, and afternoon tea experiences. Visitors can stroll the sculpture gardens, browse unique artisan shops, and enjoy performances in one of the region’s premier cultural destinations.

Conclude your visit at Josiah Henson Museum & Park, an important historical site that tells the story of Reverend Josiah Henson, whose autobiography inspired Harriet Beecher Stowe’s Uncle Tom’s Cabin. Through interactive exhibits and preserved historic structures, visitors gain a deeper understanding of Henson’s life, legacy, and the broader history of slavery and resilience in America.