Sailing to the Wye and St. Michaels on the Miles River
Sailing to the Wye River and onto St. Michaels isn’t something sailors just do once before checking it off their bucket lists. Cruisers sail here every year, in spring, summer, and fall, perhaps multiple times. You could sail to St. Michaels first and hit the Wye on your way home or vice versa. You could also spend an entire weekend in either place, depending on the vibe you seek.
Those who race in the annual Annapolis to Miles River Race over Memorial Day weekend know the route well: round those two red marks to starboard at the top of Eastern Bay (R “4” and R “6”) and head toward the Miles River. Racers keep going, of course, to find the finish line, but cruisers could choose to turn left at Bennett Point Lighthouse (giving the shoal a wide berth, keeping an eye on the chart) to head for the Wye River.
Why the Wye?
Lovely, quiet, magical: these are terms you hear cruisers use when you ask them why they choose this winding river. When choosing west or east branches, many go east for plentiful anchorage options and good kayak access at Wye Island Natural Resources Management Area (WNRM). Some cruisers never quite get there, as they enter Shaw Bay, the first protected anchorage on your right, and stay for the sunset.
Shaw Bay is also the home of a beloved annual event: the annual Shaw Bay Raftup Concert, featuring the Eastport Oyster Boys among other musicians who play from a boat to support ShoreRivers’s conservation efforts. The concert takes place the Saturday after Labor Day weekend (see the SpinSheet calendar come fall).
Those who continue up the East Wye will be rewarded with memorable gunkholing spots, such as Dividing Creek or Granary Creek, and plentiful herons, ospreys, cormorants, turtles, starry skies, and many nooks and crannies to explore by dinghy or paddle craft. If you want to step ashore at WNRM, find the kayak launch in Dividing Creek (visit dnr.maryland.gov and search “Wye Island” for a map and park details).
WNRM consists of 2450 acres managed by the Maryland Park Service for resource management, recreation, and agriculture. The island provides habitat for waterfowl populations and other native wildlife (our editor spotted a great horned owl there). Sailors may hike six miles of mostly flat trails. The School House Woods Nature Trail takes you through a mature hardwood forest while the Ferry Landing Trail leads beneath a canopy of Osage Orange Trees. Wye Island also houses a Holly Tree that is more than 290 years old.
If you venture up the west Wye, Drum Point will offer plenty of room and perhaps some breeze. Again, you may go ashore on this side of WNRM. Once you’ve had your fill of Wye River solitude, it’s time to head to civilization, Eastern Shore-style…
10 Things To Do in St. Michaels
- Dock at CBMM. Even if you prefer nights on the hook, treat yourself to a night at the Chesapeake Bay Maritime Museum dock sometime, perhaps when you need to plug in for air conditioning or heat! It’s an ideal home base for discovering the shore’s most vibrant town.
- Anchor out. Rather save your pennies for dinner in town? We get it. The St. Michaels anchorage is popular for good reason… it’s huge. If you anchor and paddle around, you’ll probably run into sailors you know. Dinghy into town or take the water taxi (hail the Harbor Shuttle on VHF 71 or (410) 819-9606), but be warned that it’s not always running in the pouring down rain (truth). If thunderstorms are in the forecast and/or you prefer a quieter spot, Long Haul Creek or just outside its mouth offers good holding.
- Stretch your legs. St. Micheals is a delightfully walkable town. If you do all 10 things on this list, you can cover it in less than a mile and a half… okay, maybe a bit more if you do #9.
- Shop local. You may not be a “shopping” type, but do stroll into a few of the local shops and art galleries for high quality gifts and art. The CBMM store is worth a peek, too.
- Grab a bite. There’s more to St. Michaels than crab cakes! The Bistro St. Michaels and Ava’s Pizzeria and Wine Bar come recommended.
- Test the flavors. Check out Justine’s Ice Cream Parlor. Walking down Talbot Street with an ice cream cone is what you’ve dreamed about all winter.
- Taste some brews. For 17 years Eastern Shore Brewing has been making award-winning beers.
- Sip some vino. Right next door to the brewery, you’ll find St. Michaels Winery where you can taste and buy local wines.
- Explore the museum. If you do nothing else in St. Michaels, do this. Walk up the steps of the Hooper Strait Lighthouse, explore the many buildings on campus dedicated to all aspects of Chesapeake life from oyster canning to recreational boating, and see the latest exhibits.
- Smile! Send a photo of your favorite St. Michaels moment to [email protected].
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