WHERE: St. Michaels, Md.

WHY: Doggy madness, great food and a killer waterfront.

HOW FAR: 70 miles from the District, or about 11/2 hours.

Serene St. Michaels goes to the dogs next Sunday when the Jack Russell Terrier Races and the Dachshund Dash take over the waterfront town. Pups that are swift of paw will gather on the lawn at the Inn at Perry Cabin, part of the annual Fall Into St. Michaels weekend.

It's a rare Russell that scurries directly to the end of the 20-foot straightaway -- more likely, the easily distracted dogs tumble on top of one another in a puppy pileup and make zigzag runs toward appreciative spectators. The Dachshund Dash proves equally comedic as the earnest short-legged sausages waddle across the turf. And, just so every dog has his day, there's the "So You Think You're a Jack Russell" heat, where racers of all sizes -- from Great Danes to pugs -- put their competitive spirit to the test. Contenders that make it through their heats are rewarded with ribbons and treats, of course.

Watching the kooky canines is free, while racing costs $15 (registration fees go to the Talbot County Humane Society). The Fall Into St. Michaels weekend also includes pumpkin carving demos, ghost tours and a costume parade, where both people and dogs turn up in everything from skeleton masks to hot pink boas.

Amid the festivities, make the most of St. Michaels's quality shopping and historic charm. Stroll Talbot Street, where Victorians sporting gingerbread trim, double porches and wavy-paned glass have been transformed into shops, galleries and cafes. New boutiques add extra style. Charisma is full of fun clothing and accessories direct from New York. Down the road is Elodie, an elegant jewel box of a shop that sells dresses, hats and scarves with a European flair.

A trip across the Bay Bridge isn't complete without a stop at the Chesapeake Bay Maritime Museum. On the banks of the Miles River, it boasts the nation's largest collection of bay artifacts (and, for the fall festival weekend, a bevy of antique hot rods). Ground zero of the museum is a screwpile lighthouse that was rescued from Hooper Strait and grounded at Navy Point. Climb to the top of this 19th-century lookout for an unparalleled view of osprey nesting and herons camping out in the marsh.

Then make your way to the harbor, an international resting spot for everything from Boston Whalers to mega yachts. One of the best perches from which to ogle boats is the Shore Restaurant & Lounge, recently launched by a husband-wife duo who have elevated dockside dining with offerings such as coriander-crusted tuna sashimi with seaweed salad and roasted Australian rack of lamb with cornbread pudding. Dine outside on the deck and watch the boats dock as the moon takes flight, and you'll have mastered an Eastern Shore tradition. Oh -- and don't forget that doggy bag.

Andrea Poe

The races are on the lawn at the Inn at Perry Cabin, 308 Watkins Lane, St. Michaels, Md., 410-745-9601. Sunday, Oct. 30, at 11 a.m.; registration at 10 a.m. Free to view; $15 per dog to race.

Road Trip maps are available online at www.washingtonpost.com/roadtrip, as are addresses and hours of operation (be sure to check before you go). Have an idea for a trip? E-mail roadtrip@washpost.com.