WHY GO IN SEPTEMBER The three-day debauchery of everything seafood (better known as the Forty-Second Annual Maryland Seafood Festival) runs September 5 to 7 ( ).  


About. 3.9 million crabs are consumed in Annapolis every year.

About. 3.9 million crabs are consumed in Annapolis every year.


Whether it’s because of the Indian summer temps, the remaining days of soft shell crab season, or the handsome sailors returning to school, Maryland’s waterside capital city is a worthy weekend getaway. The Historic District (forty-five blocks of winding streets leading down to a picturesque harbor) is pleasantly walkable. Stay in the modern Loews Hotel (126 West St., 410-263-7777, , rooms start around $250), or for more romance try any of the recently renovated Historic Inns of Annapolis ( ).

While most restaurants are kid friendly and casual, you’ll still eat well. At the sleek and bustling Kyma (69 West St., 410-268-0003, ), Greek ingredients mingle with Spanish influences. Or try modern Italian at cozy Osteria 177 (177 Main St., 410-267-7700, ), whose menu boasts items like prosciutto-wrapped pheasant and house-made gnocchi. For a totally Maryland experience, crack crabs waterside at Cantler’s Riverside Inn (458 Forest Beach Rd., 410-757-1311, ) where the trays of crabs—and mussels and shrimp and scallops and oysters—make it an Annapolis institution. If you’re not too stuffed afterward, take the leisurely three-hour Historical Culinary Walking Tour ( ), during which you’ll get a rundown of the significance of all those red-brick eighteenth-century buildings and nosh on snacks along the way.

Fall means football, and catching a Navy game is quite an experience ( )—just make sure to get tickets in advance. If sports aren’t your thing, quirk it up with a visit to the Presidential Pet Museum (51 Maryland Ave., 410-280-8850, ), where you’ll learn about our current and past presidents—with memorabilia, photos, and trivia—through the eyes of their four-legged friends.