Montgomery County, Maryland Itinerary

Activities, Northeastern US Itinerary

The Itinerary at a Glance

Montgomery County is located adjacent to Washington, D.C. making it an ideal location for groups large or small and of all ages. Enjoy culinary crossroads, rich history, and outdoor adventures – with a classic Maryland flavor.

5 Unique Experiences on This Trip

  • The Inn at Tusculum Farm
  • Woodland Manor Cultural Park
  • National Capital Trolley Museum
  • National Museum of Health & Medicine
  • The Music Center and Mansion at Strathmore

Duration: 4 Days

Available: Year-round

This Itinerary is Ideal For: Adults

Day 1 in Montgomery County

The Inn at Tusculum Farm

The Inn at Tusculum Farm, located on 500 acres, is a piece of living history. Built in 1747, it was owned by a witness to the signing of the Declaration of Independence. With three buildings to choose from—Main House, Carriage House, and Coop—The Inn’s room options, amenities, and services are ideal for small to mid-sized groups looking for a unique space.

Montgomery County is home to several agricultural gems. In 1980, the Montgomery County Council created an Agricultural Reserve, or what the locals call the “Ag Reserve.” Heralded as one of the best examples of land conservation policies in the country, the Ag Reserve encompasses 93,000-acres.

Among the working farms in the area, venture over to Waredaca Brewing Company tasting room and work your way through their extensive craft beer list.

Day 2 in Maryland

Rise and shine and enjoy brunch at The Manor at Silo Falls before heading out to Woodlawn Manor

National Capital Trolley Museum

National Capital Trolley Museum. Credit: Visit Montgomery

Cultural Park and Museum. Interactive exhibits highlight the area’s agricultural landscape, the Underground Railroad, local free black communities and the Quaker experience in Montgomery County.

Keep the history theme going with a visit to the National Capital Trolley Museum. Established in 1959, the renovated Visitor Center features exhibits on streetcar history, a display of historic trolleys, and model of streetcars and street life in Chevy Chase in the 1930s.

Established during the Civil War and home of the bullet that killed Abraham Lincoln, the National Museum of Health & Medicine is your next stop.

After a full day of exploring, it’s time for dinner at Not Your Average Joe’s – a unique neighborhood restaurant in Downtown Silver Spring. Afterward, enjoy a bit of retail fun at Ellsworth Place, or a festival at the Silver Spring Civic Center.

Day 3 in Montgomery County, Maryland

Today will be spent exploring the “downtown” side of Montgomery County along the Red Line Metro. Begin

Strathmore Mansion

Tea Pouring at Strathmore Mansion, Credit: Malerie Yolen-Cohen

by spending the morning in Rockville Town Square developing your artistic talents at VisArts.

From Rockville, ride the Red Line down to the White Flint Metro stop for Pike & Rose. Grab a meal at City Perch, enjoy a movie at iPic Theaters, or head to Pinstripes for some grown-up bowling and bocce paired with exceptional Italian and American cuisine.

One stop down on the Red Line is Strathmore. The Music Center and Mansion at Strathmore has been a beacon for performing arts since 1981. The 1,976-seat theater regularly hosts favorites like the National Philharmonic Orchestra.

Continuing along the Red Line, head to the Bethesda stop where you will be in the heart of downtown Bethesda. Dine at Mon Ami Gabi – a classic French bistro that embraces a passion for food, wine, and culture. Afterward, spend your evening shopping at Bethesda Row.

Day 4 of Things To Do in Maryland

Spend the morning immersed in art, architecture and landscape at Glenstone. A museum of modern and contemporary art, Glenstone features 59,000 square feet of indoor exhibition space in two buildings and 230 acres of serene, unspoiled landscape and sculpture.

Continue to Sugarloaf Mountain and take in the vista all around. This private mountain was used as a flag station to relay messages to Harpers Ferry and the City of Washington during the US Civil War.

This evening, travel just outside Montgomery County to the Medieval Times Dinner & Tournament for a feast and a show.

Maryland still has plenty of other places to experience and things to do, so be sure to get more Itinerary Ideas for FREE

Featured Activity

Kansas City Zoo & Aquarium

Situated in the heart of Missouri, the Kansas City Zoo & Aquarium captivates visitors with a diverse array of creatures from land and sea. From the intriguing depths of the Sobela Ocean Aquarium, home to over 8,000 marine species, to the expansive grounds showcasing wildlife from across continents, it’s a celebration of nature’s marvels. A must-visit destination for a comprehensive zoological experience.

Download Latest Issue

Recent from Activities

Montgomery County, Maryland

Montgomery County, Maryland

Montgomery County, Maryland Itinerary at a GlanceMontgomery County, Maryland is an exceptional destination for groups to visit due to its winning combination of natural beauty, historical significance, and diverse attractions. The county boasts stunning parks and...

Calvert County, Maryland

Calvert County, Maryland

Calvert County Itinerary at a GlanceLocated in south-central Maryland between a tidewater peninsula lying between the Patuxent River to the west and south and Chesapeake Bay to the east, Calvert County is one of the older counties in the state. Its mix of natural...

Subscribe for Free