Getaway: A Family-Friendly Winter Adventure in Frederick, Maryland

Baker Park in Frederick, Maryland / Photograph by William Sherman/Getty Images

Historic mansions, antique shops, and a creekside winter spectacular await in this Maryland gem, just a three-hour drive from Philly.

Day One

Frederick might be a small city, but it has a lot to offer. For an out-of-the-ordinary stay downtown, check into Marriott’s new Visitation Hotel (rooms from $309), housed in a former Catholic girls school. The rooms combine old and modern, with thoughtful nods to the property’s past in the decor. Walk to Carroll Creek Park, admiring the 19th-century mansions and rowhomes — suitably decked out for the season — along the way. Catch the sunset, when a fleet of decorated boats light up the waterway for Frederick’s Sailing Through the Winter Solstice. The spectacle runs through March and doubles as a fundraiser for the city’s nonprofits. Then pop into the Wine Kitchen on the Creek for a flight and cheese board, or simply stay for dinner. End the night with a cocktail made with locally distilled spirits at McClintock’s Back Bar.

The whiskey at McClintock’s Back Bar is distilled right next door. / Photograph courtesy of McClintock Distilling

Day Two

Start at Gravel & Grind, a cafe and bike-rental shop, with coffee and toast — try the labneh, pistachio, and candied orange topping — or waffles (available on weekends). If it’s not too chilly, rent some wheels and cycle out, riding through scenic Baker Park to Carroll Creek Covered Bridge, a smaller example of the structures at Utica Mills, Loy’s Station, and Roddy Road in northern Frederick County. (Those covered bridges are within a half-hour drive.) Pick up a kati roll at Hinzi’s Kitchen, a Pakistani-Mediterranean fusion spot, and wash it down with a pint at Olde Mother Brewing Co. or one of several other breweries downtown, like Attaboy Beer or Idiom Brewing Co. Prefer an outdoor experience? Go hiking at Cunningham Falls State Park to see Maryland’s tallest cascading waterfall, standing 78 feet high. (Just remember to bundle up!) Back at the hotel, enjoy dinner in the old chapel (complete with stained glass), now the hottest restaurant in town: Wye Oak Tavern, from Frederick-born celeb chefs Bryan and Michael Voltaggio.

The new Visitation Hotel in Frederick, Maryland / Photograph by Ron Blunt

Day Three

Grab a sourdough bagel made with regional grains — including from Pennsylvania’s Small Valley Milling — at Twin Bears Bakery. Everything’s excellent, but you can’t not get the Old Bay cheddar bagel. Next, go shopping on Market and Patrick streets. Channel your inner Martha Stewart at new kitchenware (and more) store Le Voyage Market, and buy a locally made mug at the Potters’ Guild of Frederick. Explore Emporium Antiques at 112, and peruse mid-century furniture at Vintage MC. And broaden your mind at Curious Iguana, a welcoming bookshop with a fantastic selection for kids and grown-ups alike. On your way home, take a 10-minute detour to Dutch’s Daughter. Order the cream of crab soup downstairs at the medieval-style Dutch’s Dungeon for a memorable end to your trip.

The seared ahi tuna at the Wine Kitchen on the Creek / Photograph courtesy of Tovala

Family Time

Fun ideas to keep the kids occupied, no matter the season

1. Inspire imagination at Dancing Bear Toys and Games, an “unplugged” electronics-free shop offering science kits, puzzles, plushies, and more.

2. Take playtime to Sophie & Madigan’s Playground, an inclusive space with adaptive swings, tactile panels, and quiet zones just 10 minutes from downtown.

3. Ride the historic Walkersville Southern Railroad on tracks built by the Pennsylvania Railroad Company. Special events include Santa Trains that run every weekend through Christmas.

4. Play Picasso at the Delaplaine Arts Center’s “Art Cart” stations with supplies to create a masterpiece. Leave your kid’s artwork to be displayed, or keep it as a souvenir.

Published as “Escaping to Frederick” in the December 2025/January 2026 issue of Philadelphia magazine.