Published: October 2009Best Adventure Towns
Annapolis

Annapolis, Maryland

Plan a long weekend getaway with our Annapolis adventure guide, featuring great outdoor escapes, where to stay, and where to eat. Then chime in with your picks.

Photograph courtesy of visitannapolis.com

Pop. 36,300
GPS: 38°58'N 76°30'W

Maryland’s colonial capital is the major recreation port of Chesapeake Bay and home to the U.S. Naval Academy. Blow off steam kayaking, sailing, wind-surfing, or go crabbing for your dinner.

Your Turn: Tell us about your favorite Annapolis adventures, restaurants, and hotels in the comments section below.

PLAY
The Chesapeake is flooded with ships of all shapes and sizes and with a little chutzpah you can kayak right alongside them (kayak rentals $15 an hour; annapoliscanoeandkayak.com). But if the hustle and bustle of imposing boats and lighthouses becomes too much then head to Quiet Waters Park for a more soothing paddle (aacounty.org/RecParks/parks/quietwaters). Want to try your hand at crabbing? Ask a park ranger! Matapeake County Park can be hit or miss depending on the season (parksnrec.org), so consider renting a boat at Sandy Point State Park and up your chances with a little mobility (dnr.state.md.us/publiclands). Or just time your visit to coincide with the annual all-you-can-eat August crab feast (annapolisrotary.com/crabfeast.asp) and forgo the work.

EAT
Chick and Ruth’s Delly, at 165 Main Street, is a local institution in business now for 40 years. Show up early for the Pledge of Allegiance, and stick around all day washing down your "Colossal" reuben with a six-pound shake—and win a t-shirt if you finish both in an hour (chickandruths.com).

SLEEP
The Inn at Horn Point has preserved the original features that made it a cozy home when it was built in 1902—a big wrap-around porch, double bay windows, and pine-wood floors—and added the modern amenities that now make it a comfy weekend base camp (doubles from $149; innathornpoint.com).

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