Fall Weekend Getaway: Annapolis, MD

Think cobblestone and crisply uniformed Navy midshipmen — the sailing capital of the U.S. is happening enough to keep you busy, but quaint enough to feel like an escape. (All just a two-hour drive from Philly.) Here’s our fast and loose tour of Annapolis, Maryland

Friday, 6 p.m.: Check-in to a Historic Queen room at the Governor Calvert House (home of governor Charles Calvert, circa 1720), one of the three Historic Inns of Annapolis.

Friday, 6 p.m.: Check into a Historic Queen room at the Governor Calvert House (home of governor Charles Calvert, circa 1720), one of the three Historic Inns of Annapolis. Enter room and marvel at the cute sitting area, the reproduction antiques, the four-poster bed … and the modern bathroom with spacious tub (58 State Circle, 410-263-2641, historicinnsofannapolis.com).

[sidebar]8 p.m.: You’re hungry, but too tired to walk far. Head just around the block for superb Irish nosh at Galway Bay. Do try the crab cakes, cabbage wraps, shepherd’s pie and Guinness-fried oysters (61-63 Maryland Avenue, 410-263-8333, galway2006.com).

9:30 p.m.: Sated, or more likely, stuffed. Head to bed. (Or, night owls can stroll Main Street to scout shops to check out during the day, or pop in for a brew at any of the many, many pubs.)

Saturday, 9 a.m.:
Get an early start and see some history. (Grab a bite from the complimentary breakfast spread on your way out.) Just outside is the State House (circa 1772) with its massive dome; it’s the oldest State House still in legislative use, and served as the U.S. Capitol for a brief period from 1783-1784 during a meeting of the Continental Congress (100 State Circle, msa.md.gov/msa/homepage/html/statehse.html).

Also check out the William Paca House (constructed in the 1760s) and gardens; the house is a five-part Georgian residence, historically restored to the way Paca, a signer of the Declaration of Independence and once-governor, likely had it (186 Prince George Street, 410-267-7619).

1 p.m.: Stop for lunch at Chick and Ruth’s Delly, an Annapolis landmark, where the sandwiches are named after politicians, the owner does magic tricks, and, every morning, the whole place, customers included, holds hands over hearts to recite the Pledge of Allegiance (165 Main Street, 410-269-6737, chickandruths.com).

3 p.m.: If it’s not sailing season (November through March), spend the afternoon shopping along Main Street and environs. On your way back to the Calvert House, don’t miss the Marion Warren Gallery, which houses the photographer’s magnificent capturings of life along the Chesapeake from the 1940s on (14 State Circle, 410-280-1414, mewarren.com).

If it is sailing season (April through October), climb aboard a Schooner Woodwind sunset cruise (3 p.m. to 5 p.m.). The fleet consists of two identical 74-foot schooners, one of which (the Woodwind II) was used in the film Wedding Crashers. On deck, you’ll enjoy jokes from your exuberant captain and be offered a turn at the wheel (great fun for kids; a fabulous photo op for grownups). If it’s not sailing season, it’s probably holiday season, so buy a gift card for the spring! (80 Compromise Street, 410-263-7837, 800-638-9192, schoonerwoodwind.com).

Or, if you really want to get your sea legs, learn to sail with a course from the Annapolis Sailing School. (7040 Bembe Road, 410-267-7205, annapolissailing.com.)

6:30 p.m.:
Time for dinner. For something trendy, try ocean-themed Kyma (pronounced “kee-mah” — “ocean wave” in Greek), Annapolis’s take on Philly’s favorite food trend: Spanish-style tapas, but here with Greek and Chesapeake influences (69 West Street, 410-268-0003, kymarestaurant.com). Or, for something more traditional (like 18th-century traditional; our Ben Franklin dined here once) try the Treaty of Paris in the Maryland Inn, the most storied restaurant in town (16 Church Street, 410-216-6340, historicinnsofannapolis.com).

8:45 p.m.: Skip the standard history tours and opt for something way more fun — a ghost tour, plus drinks! — with Ghosts of Annapolis Tours’ Haunted Pub Crawl. Hear about the bride who committed suicide when she leapt the window of the Maryland Inn. Learn about the strange bedpost poking through the ceiling in the basement of the Ram’s Head Tavern. (Besides, everyone knows it’s far easier to see spirits after a few pints.) (443-758-5345, 800-979-3370, ghostsofannapolis.com).

Sunday, 10 a.m.: You don’t have to go far for good a.m. fare — Harry Browne’s, just next door, offers a delicious “Champagne Brunch” on Sunday mornings for just $17, with buffet and à la carte options. Grab a window table for a great view of the State House (66 State Circle, 410-263-4332, harrybrownes.com).

11 a.m.: Tour the U.S. Naval Academy. Learn the stories behind the statues — like the figurehead of Tecumseh, once heading the Delaware, which was sunk during the Civil War. (Today, he’s an idol for midshipmen, who offer him prayers and pennies for good luck on tests or on game day.) Buy touristy Navy gear at the gift shop to commemorate the weekend (121 Blake Road, usna.edu/visit.htm).

1 p.m.: Ice cream will help ease the depression you’ll no doubt feel leaving. Get some at the Annapolis Ice Cream Company, where there are more than 35 homemade flavors — like the very popular apple pie, made with chunks of delicious, gooey, fresh-baked pie (196 Main Street, 443-482-3895, annapolisicecream.com).