Whether one sails into town, hops aboard a rickshaw or cycles down Main Street, there's plenty to see and do.
Population: About 1,400 full-time residents
Main attraction: Maritime culture. Check out the Waterman's Museum at Haven Harbour Marina, 20880 Rock Hall Ave., 410-778-6697.
Small-town surprise: Rickshaw rides.
Eat here: Waterman's Crab House Restaurant has some of the best sunset views on the bay – and you can come by boat and dock while you dine. 21058 Sharp St. 410-639-2261, watermanscrabhouse.com. For breakfast, including coffee and pastries, try Java Rock, 21309 Sharp St., 410-639-9909.
Stay here: Inn at Huntingfield Creek is a B&B on a lovely farm estate on the waterfront. Rates start at $179 per night. 4928 Eastern Neck Road, 410-639-7779, huntingfield.com.
Don't miss: Soda fountain treats at Durding's Store at the corner of Main and Sharp streets, 410-778-7957, sailingemporium.com/durdings.
Info: Call 410-639-7611 or go to rockhallmd.com or kentcounty.com
St. Michaels, Talbot County
Fictional Mayberry meets The Hamptons in this picturesque 17th Century village, situated along the Miles River on the Eastern Shore.
Population: About 1,193
Main attraction: The Chesapeake Bay Maritime Museum overlooks the harbor. Its 18-acre grounds include a working boatyard and a historic lighthouse. 213 N. Talbot St., 410-745-2916, http://www.cbmm.org.
Small-town surprise: Carriage rides along Talbot Street, the town's main thoroughfare lined with shops, art and antiques, lodging.
Eat here: Akai, from the Japanese word for red, serves up sushi and is one of the town's new restaurants. The chefs make everything in house, using the freshest ingredients possible. 402 South Talbot St., 410-745-8099, akaistmichaels.com.
Stay here: The Inn at Perry Cabin. You'll see yachts and bikes alike at this elegant 19th century manor. Chic accommodations, a posh spa and gourmet restaurant, plus stunning sunsets over the water. 308 Watkins Lane, 866-278-9601, perrycabin.com.
Don't miss: Take a scenic bike ride along the 26-mile Oxford/St. Michaels trail or enjoy a scenic cruise aboard the Patriot, a 65-foot steamboat replica in operation since the 1960s.
Info: Call 410-770-8000 or go to tourtalbot.org
Oakland, Garrett County