Top 5 Cruising Destinations on the Chesapeake Bay

sunset creek


Fall sailing is absolutely the most enjoyable time of the year to cruise the Chesapeake Bay.  After Labor Day, the temperatures start to cool and the wind begins to build.  The water is still warm, so even on chilly days the breeze is pleasant.  The small towns that sprinkle the bay shoreline revert back to sleepy, picturesque hamlets after the summer tourists clear out. During the week, there are dozens of creeks and rivers which can be explored with only yourself as company and the weekends are less crowded.  When the leaves start to turn, the shore line becomes a mass of oranges, golds and reds accented by the wildlife that still abounds this time of year.

Having been born and raised in Annapolis, I’m often asked the same question,  “What are the best places to cruise on the Bay?”   All of my favorite locations are within easy reach of boats departing from the Annapolis area.  Perhaps another time, we can explore areas further north and south.  Here are a few of my favorites.  I hope you have the opportunity to explore these areas as well.


Stunning views and sunsets are frequent on the Chesapeake.

  1. Magothy River – Eagle Cove

    Don’t let the tricky looking channel dissuade you from this lovely spot.  Located just behind Gibson Island, you will pass stately waterfront homes on your way to the entrance.  The entrance is well marked and the charts are pretty accurate.  Simply stay in the channel and as you pass the sand bar on your right and make your way into the cove.  On your left is a beautiful horse farm.  Grab a cocktail, sit back and relax while watching the horses graze. See if you can spot the building with the large tree growing out of the center.

  2. Swan Creek in Rockhall

    Rockhall is a laid back town that is best enjoyed on the weekdays or in the fall.  The town offers a trolley and for a small fee, you can travel to and from the marinas and town. Be sure to check the schedule for days it operates.  Most of the marinas on Swan Creek are at the opposite end of town and offer various amenities including bikes.  It is a fair hike into town made easier with bikes, especially if you are buying groceries.  In town you’ll find numerous shops, cafes, restaurants featuring local fare.

  3. Worton Creek

    Worton Creek proper doesn’t have tons of anchoring space once you get truly in the creek (past the visible sandbar).  However, that’s not where you want to go anyway.  As long as the weather will allow, anchor “outside” the creek off the north shore, right before you enter the creek’s channel.  Here you will find a lovely spot to drop the hook.  Open to winds from the west and south with views down and across the Bay.  On the north shoreline, you will likely spot numerous Bald Eagles soaring above the trees.  Further out on the north shore where the bluffs are high and the shore juts into the bay, is a really cool driftwood beach. From this beach, you feel like you could see all the way down to Norfolk.  Much  of what floats north in the bay will land on this beach and makes for fun exploration of the shoreline.


    Cormorants in the shallows inside Worton Creek

  4. Wye River 

    Wye River circles Wye Island which is sparsely populated and part of the Natural Resources Management Areas.  If you have a kayak on board, THIS IS THE place for exploration.  There are miles and miles of shoreline, small coves only accessible by small craft.  Deep water and a well-marked channel make this an easy to reach destination.  There are numerous anchorages that provide either open areas on those hot, still evenings or hurricane holes where even 40 knot breezes will cause only a slight stir.  Check your charts or cruising guide for access from the water to the numerous hiking trails on the island.

    On your way…


    Bloody Point Lighthouse

    Bloody Point Bar Lighthouse – Eastern Bay

    Entering Eastern Bay on your way to Wye River or St. Michaels you will pass Bloody Point Bar Lighthouse.  Constructed in 1881, it was designed to withstand the ice flows which, at the time, were destroying all the screw pile light houses such as the one still standing: Thomas Point Light House.  In the Chesapeake Bay Maritime Museum photo below, you will see another example of the screw pile light house, Hoopers Straight Light, which was removed from the Bay and restored at the museum.  Bloody Point Light was a manned light house until 1960 when an explosion and fire forced the crew to abandon the lighthouse.  The lighthouse was sold to a private party who is hoping to restore it.  Unfortunately, earlier this year when we passed by we noticed a large hole in the side of the structure that had not been there the previous fall.

    As a child, whenever we passed by the bright red lighthouse, my father used to make up stories of pirates and bloodshed in that area..  How could that not be true with a name like Bloody Point!

  5. St. Michaels

    If you have never been to the quaint town of St. Michaels,you need to put this on your cruising agenda.  My favorite time of the year is in the fall.  Check St. Michael’s town calendar for events including the Fall Festival in October.  The pumpkin carving is amazing.  The scarecrow contest runs for two weeks.  The scarecrows are attached to light poles throughout the town for you to vote on your favorite.  The town features a number or restored historic houses.  For about $10,  the town museum offers a guided walking tour and it includes access to the St. Michaels Museum.  There are 3 large marinas as well as anchoring outside of the entrance, which is served by a water taxi.  The Chesapeake Bay Maritime Museum has exhibits and activities all year long for young and old.  This museum truly captures the history and spirit of the towns and people of the Bay area and is definitely not to be missed.  There are plenty of restaurants and cafés to get a meal and quench your thirst.


    Chesapeake Bay Maritime Museum from the water


    Written by Vicky Lohman, Fufillment Manager at APS.

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