One of the places that I keep returning to is New Market, MD.
Just a few minutes up I-70 (from Baltimore), New Market calls itself the Antiques Capital of the World. Whether true, or not, there are a lot of antique and boutique-y stores along its main street, and it's a pleasant afternoon walking up one side and back down the other. The sidewalks offer plenty of shade to make hot days bearable, and the residents seemingly have consciously made an effort to emphasize the picturesque aspects of their homes.
One of my favorite stores offers a mix of antiques and jewelry that make browsing fun. I rarely leave this store without making a purchase -- and try to time visits for upcoming special events for which I'll want small gifts to give.
Established in 1793, New Market boasts a mix of colonial and Victorian-era homes, along a tree-lined main street that represents the best of old-time, small town Maryland. New Market holds two annual festivals that highlight the town's historic past. The "A Day in New Market" festival is held annually on the first Saturday in May. "Christmas in New Market" is held on the first Saturday in December every year as well. Both festivals celebrate the traditional life of 18th and 19th century residents.
Getting there: Take Exit 62 off of I-70. About 15 minutes east of Frederick; 30 minutes west of Baltimore.
Hours: Tricky -- all the stores keep different hours. Weekends almost sure to be open.
Dogs: Clean up after your pooches if you bring them along -- but they may not be welcome inside the stores.
Updated May 2018.