St. Michaels MD Getaway After the Chesapeake Bay Swim

2025 Great Chesapeake 4.4 Mile Bay Challenge

My bestie, Diane, decided it would be fun to swim the entire 4.4-mile length of the William Preston Lane Jr. Memorial Bridge— better known to East Coasters as the Chesapeake Bay Bridge-in the 2025 Great Chesapeake 4.4 Mile Bay Challenge held on June 8, 2025. Naturally, we went to cheer her on… though “cheer” might be generous, considering we basically waited at the end.  Even three people who were on the same Ecuador tour came from Boston and New Hampshire.  You know New Englanders-they love a celebration.

As all good events begin-we started at Dunkin’.

The day before the race, as we crossed the Chesapeake Bay Bridge headed east, you couldn’t see the shore on the opposite side because of the rain and fog. When we thought about how long the swim was, it looked really, really far.

The event is timed during slack tide, which means the tides aren’t trying to suck you out to sea, but don’t worry—Mother Nature still brings the drama, in wind direction, wave size, and trying not to swallow half the Bay which is blowing in your face with each breath.

The race starts at Sandy Point State Park on the western shore. Swimmers head east, make a right turn to go between the two bridge decks, power through the main shipping channel (yep, where the big boats go), and—about 700 yards from the finish—duck under the south bridge span to land on a tiny beach on Kent Island. All of this must be completed in under 3 hours and 45 minutes—because at that point, the big ships get cranky and want their lanes back.

Now, the morning of the race, there was a small craft advisory. Translation: “Hey, kayaks and humans—good luck out there!” Forecasts called for 1- to 2-foot waves in the swimmers’ path. Out of 621 registered athletes:

481 bravely walked into the Bay,

48 were plucked out mid-swim, defeated, and 

433 made it to the other side, victorious and depleted.

Most swimmers said mile three felt like getting tossed around in a giant washing machine. If you stopped swimming, you reversed. One moment you’re headed to Kent Island, the next you’re returning to Sandy Point.

But guess what? Diane finished. Not just finished—she crushed it. Fourth in her age group! Although, she also reported “One and done. It was hard.”

St Michaels, Maryland

After the swim, we made our way to St. Michaels, a harbor town so charming it feels like it was designed by a Hallmark movie location scout.

Nestled on Maryland’s Eastern Shore, it’s known for its maritime history, Victorian architecture, and a main street lined with boutique shops, art galleries, and eateries housed in 19th-century buildings.  There are T-shirts for sale with a crab and Old Bay on it in most shops.  (Ironically, I am allergic to Old Bay, and servers found odd that I would vacation there since it is served on everything.) It is dog friendly, and my bestie’s arthritic 13-year-old Springer Spaniel accompanied us in a stroller to restaurants.  At restaurants, servers brought our food, and a bowl of water with ice cubes for the dog. And the food served was very tasty.

We rented a house on Long Haul Creek, about a mile from town—close enough for convenience, far enough to justify the ice cream we ate. The house was decked out with toys: two kayaks, a canoe, lawn games, a crab trap and Adirondack chairs around the fire pit. A screened porch kept the mosquitoes out and the political discussions in. We had visits from a friendly cardinal, bunnies, a fox, deer, a snake, cow nosed rays (who stayed in the water) and a blue heron who fished from the dock.

No one was in the mood to cook (vacation rule #1), so we either walked or rode bikes into town for meals. We caught up on reading and lounging. Honestly, it was the kind of getaway where the biggest decision was kayak, bike ride or nap—and either choice was a win.

We embarked on a two-hour sail aboard the Salina II, a restored 1926 sailboat that looked like it had just stepped out of mid nineteenth sailing history. Departing from the Harbour Inn, we set off into the Miles River. At the helm was Captain Iris, who is basically the St. Michaels Beyoncé of historic sailboats. She skippers the Salina II, which was originally commissioned by her grandfather.  It is the largest surviving catboat, which means it has a wide, shallow hull, a single forward mast, and a sail setup called “gaff-rigged,” meaning the sail is four-sided and rigged at the top with a spar, which looks like a crane’s arm.

Views from the Salina II

The boat itself was a floating work of art—with high gloss varnished mahogany and polished brass.  Captain Iris educated us on wind factors, water temperatures, and pressure systems. It was two hours of gentle breezes, scenic views, and deep appreciation for the fact that we didn’t have to paddle. 

We returned home rested and ready for our next adventure.