The Chesapeake Bay is nearly 150miles long and over 20 wide at its broadest point. It is home to major ports of Baltimore and Annapolis in the upper bay, and the Naval yards of Norfolk at its Atlantic entry. Untethered entered the Chesapeake after 1,600NM and 8 days transit from the Virgin Islands with a full day sail remaining to arrival in Annapolis. After landfall and departure of the crossing crew, Untethered began a week of exploration of the countless bays and small harbors that define the Chesapeake coast line.

First stop is the town of Oxford on the eastern shore up the Tred Avon River. Oxford has a long history dating back to the 1,600’s and an important place in the American Revolution. Today Oxford is the perfect East Coast Harbor hamlet, with a population of ~650 you are transported back in time when life had a different pace. Untethered comes to dock two blocks off main street with a short walk to Country Inns with broad porches and thoughtfully prepared meals. At the center of town is a large central park with an expansive view of the Bay and a dozen well placed benches where locals and visitors gather every evening to watch the sun set over the bay to the west. After 8 days at sea, Oxford becomes the perfect place to recharge, unwind and orient to shore once more. We quickly find our favorite porches for a meal and reflection; The Robert Morris Inn (site of James Michener writing of Chesapeake) and at the far end of Main Street, The Oxford Inn and Pope’s Tavern.

After three peaceful days at dock in Oxford, shore lines are cast once again for the short sail south to Cambridge, another historic East Shore harbor and town. Wind and heading allow the Spinnaker to fly from Untethered’s bow sprit as we navigate the Choptank to the town dock. Cambridge is another picturesque and historic Maryland town. Once a center for Tobacco production and an important stop on Harriet Tubman’s Underground Railroad, Cambridge is now a quiet coastal destination.

After a few days frequenting the streets and cafes of Cambridge, Untethered casts off for the start of our journey north up the Chesapeake to the C&D Canal (Chesapeake and Delaware), our passage for the continued journey North. As we push North up the Bay our next step is the town of St Michaels. St Michaels is an active summer vacation resort town and a pace quicker from the last few days. With a population of ~1,000 St Michaels is certainly a small harbor town but surrounded by a busy coast of vacation homes and boat docks. Untethered lands in the center of this small harbor town and just a block off Main street. Main Street is filled with small shops, Cafes and Restaurants along with the local Craft Brewery and an outlet for Maryland Wines. St Michaels played an interesting role in the War of 1812, when townsman famously avoided a nighttime attack from the Bay when they darkened the town and set lanterns in the trees on hills above town, successfully directing the cannon onslaught well above the town center. After two days onshore Untethered pushes off the Dock for the journey further north up the Chesapeake.

Aft winds favor the Spinnaker and Untethered sails the center line of the Bay north, passing under the Chesapeake Bay bridge with a full Spinnaker and 9Knts of speed we continue north and elect an overnight in one of the countless quiet bays that line both sides of the Bay. We drop anchor as the sun is setting in Worton Creek, just of the small village of Chestertown.  A long day begins at sunrise as we pull anchor and head further north up the Bay, heading for the C&D Canal. The C&D has been the lifeline and supply line between the Delaware Bay and the Chesapeake for nearly 200 hundred years. The idea for the canal was formed in the late 1700’s by noted Philadelphian Benjamin Franklin, along with others, as a way to simply connect Philadelphia and Baltimore as well as shorten the passage from New York and eliminate a long stretch of coastal navigation in the Atlantic. The idea became reality in 1829 when the canal officially opened followed by millions of tons of freight over decades. In 1920 the canal was adopted by the US Government and became part of the large system of Intercoastal Waterways. All this history was but background as Untethered steamed smoothly up the northern reaches of the Bay in the early morning light as we turned seamlessly east into the canal and proceeded up her 14 mile length. At only 500 feet in width it felt like a cruise thru the countryside of Maryland as we pushed across the Delaware and began the rest of our journey north that would eventually take us to Manhattan, Long Island, Cape Code and the Coast of Maine.