There are a lot of reasons you may enjoy cruising the Chesapeake, and St Michaels has something for everyone who does. Second only to Annapolis, St. Michaels is probably the most visited town on the Chesapeake, and with good reason. History, shopping, architecture, food, lodging, marinas, anchorages and wildlife. Not only does St. Mikes have much to offer, but it is also compact. Everything is in easy walking distance of the waterfront landing. No other town has so much so well laid out and convenient to boaters.
The picturesque approach to the town though Eastern Bay and up the Miles River leads past some of the Bay’s most serene and lovely anchorages. There are few navigational challenges getting to St. Michaels from the Chesapeake, such as the shoal the middle of the Miles River near the Wye River (but it is well marked). The shoal off Fairview Point at Leeds Creek has caught a few unwary boaters who were too focused on the Hooper River Lighthouse and the scenic approach to the town and failed to respect the green day mark #1.
There are three marinas catering to vessels of all sizes. Most weekends the number of visiting boats outnumbers the available slips, and you will find boats anchored at several anchorages, all conveniently close to the floating dinghy dock along Cherry St. next to the Crab Claw Restaurant. If you arrive early enough, you may be lucky enough to find a spot in Fogg Cove, but be sure to respect the channel, as boats that infringe on it are likely to get a visit from the local constabulary and be asked to move.
The other well-protected anchorage is in the cove at Parrot Point, which can hold three to five boats depending upon how they fit. Either cove has you anchored close to the Chesapeake Bay Maritime Museum (CBMM), and the view from your cockpit of the traditional Chesapeake workboats and colonial waterfront buildings of the museum will carry you back in time to a bygone era when fleets of working watercraft plied the Bay and collected and transported the harvest.
If the inner anchorages are full when you arrive, you will see a fleet of boats anchored in the roadstead outside the harbor. This anchorage here is good except perhaps in a strong northerly wind. In season there is a water taxi service for the boats here in the outer harbor. You will enjoy a beautiful sunset over the town as the evening progresses. If the wind kicks up, you will find comfortable anchorages in Long Haul Creek or Leeds Creek, worthy places to visit in their own right.
For most cruisers, a visit to CBMM is a must stop. The museum’s mission is preserving the heritage of the Chesapeake Bay region, especially the craft, history, and culture of the people who lived and worked these waters for hundreds of years. The museum library is the repository of the works of Howard Chappell. The library holds more than 10,000 volumes of history of American working small craft. Scholars from around the world have spent time working and researching at the museum. The fleet of more than 80 Chesapeake Bay working watercraft is the largest such fleet in any museum. There are a dozen floating and operating working craft at the docks of the museum, a collection maintained by staff and volunteers at the museum’s active operational marine railway and boatyard. The museum has more to display than one can absorb in a day. That leaves reason enough for another visit to the town later in the season.
After docking your dinghy at the Cherry Street dinghy float, head up to Talbot Street. The shops and stores range from antiques to touristy, clothing to jewelry, and intermixed are restaurants of every type. In good weather, you can dine in one of the outside eateries. In all weather you will find the local crowd at the Carpenter Street Saloon. If you take one of the small streets to the left, you can walk by the homes in the old part of town. Here the trees arch over the roads making this a pleasant walk even in midsummer. Many of these homes date from the Colonial era, and all are well maintained and beautifully landscaped. With a little research you can find the Cannonball House on Mulberry Street where a cannon ball from the famously deceived British fleet shelling the town in 1813 hit a house. It is said that it came through the roof of the house, rolled across the attic floor and down the stairs startling the occupants.
It would be hard to try and list all of the unique and interesting shops along Talbot Street, but one in particular that we visit is a, the purple building with green trim, where you will find interesting and creative works by local and national artists. Since we cruise with our sea beagle Consuelo, we always make a stop at
Flying Fred’s pet boutique to get her a treat before we head to the boat. After several hours of exploring the village, we are ready for ice cream.
Jo-Jo’s Cupcakes is a great place to stop, cool off, and get your bearings. The last stop before we go to the boat is Albertsons Market for fresh produce and supplies. This is the most convenient grocery market in any town along the Chesapeake, only three blocks from the dinghy dock.
St. Michaels attracts many visitors with numerous, varied events. From early April well into November, and even for a spectacular holiday parade, there seems always to be something happening in this Eastern Shore gem.
St. Mike’s To Do List
Overnight stay at the Chesapeake Bay Maritime Museum. For a unique experience, museum members can stay aboard their boat in a slip at CBMM. This option is available to members at the Mariner level and above.
Watch the log canoes. Boaters may witness the wonderful spectacle of Chesapeake Bay log canoe racing in the Miles River June 27-28; July 25-26; and September 20.
Antique and Classic Boat Festival. During the weekend of June 19-21, the museum docks will be filled with classic wooden craft from varnished runabouts to working deadrise boats. The fleet includes “Classic Plastic,” including some beautifully restored examples of early fiberglass boats.
Watermen’s Appreciation Day. August 9. Steamed crabs and beer, what more do you need to know? If you have not witnessed one of the famous Chesapeake Bay workboat boat docking contests, this is a good one to watch.
Mid Atlantic Small Craft Festival. October 3-5. Hundreds of small boat builders will display and demonstrate their craft and their crafts.
--by Tom Hale
The picturesque approach to the town though Eastern Bay and up the Miles River leads past some of the Bay’s most serene and lovely anchorages. There are few navigational challenges getting to St. Michaels from the Chesapeake, such as the shoal the middle of the Miles River near the Wye River (but it is well marked). The shoal off Fairview Point at Leeds Creek has caught a few unwary boaters who were too focused on the Hooper River Lighthouse and the scenic approach to the town and failed to respect the green day mark #1.
There are three marinas catering to vessels of all sizes. Most weekends the number of visiting boats outnumbers the available slips, and you will find boats anchored at several anchorages, all conveniently close to the floating dinghy dock along Cherry St. next to the Crab Claw Restaurant. If you arrive early enough, you may be lucky enough to find a spot in Fogg Cove, but be sure to respect the channel, as boats that infringe on it are likely to get a visit from the local constabulary and be asked to move.
It would be hard to try and list all of the unique and interesting shops along Talbot Street, but one in particular that we visit is a, the purple building with green trim, where you will find interesting and creative works by local and national artists. Since we cruise with our sea beagle Consuelo, we always make a stop at Flying Fred’s pet boutique to get her a treat before we head to the boat. After several hours of exploring the village, we are ready for ice cream. Jo-Jo’s Cupcakes is a great place to stop, cool off, and get your bearings. The last stop before we go to the boat is Albertsons Market for fresh produce and supplies. This is the most convenient grocery market in any town along the Chesapeake, only three blocks from the dinghy dock.