100 Things to Do in Annapolis and Eastern Shore Before You Die

100 Things to Do in Annapolis Before You Die front cover

Why I Wrote This Book

My family moved to Annapolis when I was 13, and my tenderest coming-of-age memories are here. Best friends. Summers on our sailboat. High school parties. First job. I went to college nearby, and waitressed in Ocean City during summer break. I moved to NYC after college, but Annapolis was always home, albeit for shorter bits of time: Christmas break, two weeks in summer, spring or fall weekends as work and life allowed. I loved those visits; they were never long enough.

In 2018 I moved back to Annapolis, and found my hometown familiar but different. I wanted to get to know it on a deeper level, so I went to my go-to: writing. I spent six months researching this book, driving all over Annapolis and the Eastern Shore, talking to old friends and making new ones, revisiting longtime favorites and searching out surprises. And in the process, I fell madly in love with the Chesapeake Bay region all over again.

What I Discovered

The book is broken up into five categories: Food, Culture, Sports, Nightlife and Shopping. So many of these overlap. Sailing is a sport, but also part of our culture. Oysters and crabs are on almost every menu, but also key to our past. So much of what we have here ties into other things, creating the interconnected web of Chesapeake Bay culture. The sense of place we have here is deep and pure, and stretches back 400 years.


A Few of My Favorite Things

Some of my favorite experiences while researching the book:

  • Driving the back roads near Salisbury with my sister-in-law Barbara, searching out an old Mason-Dixon marker (#24)
  • Taking the mail boat out to Smith Island on a blustery winter day, listening to the locals share gossip as they returned home from the mainland (#55)
  • Raising my paddle for the winning bid on a vintage wicker elephant stand in Crumpton (#97)
  • Beating my boyfriend at tabletop shuffleboard after doing the Booze Trifecta in St. Michaels (#24)
  • Heading out on a sunset sail with visiting friends and watching their joy as they experienced the Bay for the first time (#51)