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The Group Travel Leader Going on Faith Select Traveler

Small and Charming in Maryland

Driving around Maryland, it’s easy to forget the state has any cities. Its thousands of miles of waterfront, Appalachian mountain plateaus and historic farmland all shelter small towns oozing with so much warmth that you can’t believe you were in Baltimore just an hour before.

These small Maryland towns make great settings for small meetings.


St. Michaels

In the necks, an area of Maryland’s eastern shore marked by its hundreds of narrow peninsulas snaking out into the water like capillaries, St. Michaels is the unofficial hub of Chesapeake maritime culture.

Its 10-building Chesapeake Bay Maritime Museum, which includes the 1879 Hooper Straight Lighthouse, Fogg’s Landing Wharf and a 1920s sailboat on an 18-acre property set along 2,000 feet of shoreline, offers dozens of diverse rental options, all the way up to a lawn for a 350-seat reception. Groups can also try their hands at shipbuilding skills after touring the facility, which includes opportunities to meet working watermen and boat restorers.

St. Michaels has also become a local mecca for small-batch alcohol production, with Eastern Shore Brewery, St. Michaels Winery, and Lyon Distilling Company all close by and available for tastings, tours and private rentals.

Garrett County

In the Allegheny Mountains, Garrett County is the place to go when you want to get away from it all and immerse your group in nature without driving too far.

“We’re an outdoor recreation area, but you don’t have to be superactive,” said Sarah Duck, director of tourism and marketing for the Garrett County Chamber of Commerce. “Our area also lends itself to team building really well, with the outdoor recreation activities and the relaxed small-town setting. If someone wants to have a retreat, it’s a good space to do that.”

Garrett County shines especially in the winter with Wisp Resort, Maryland’s only ski resort, which, in addition to the slopes, has plenty for the ski averse. Visitors can take the year-round mountain coaster or snow tube down the mountain, an activity that combines the best of sledding and river floating with a moving walkway to ease repeat trips up the hill. The resort offers 40,000 square feet of meeting space, Segway rides and a ropes course for team building.

In the winter, small groups can take sleigh rides and horse-drawn-carriage rides. Summer brings both flat-water and whitewater rafting, boating on Deep Creek Lake, ecotours with a professional wildlife photographer and evening hayrides culminating in bonfires.