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Chesapeake City and Havre de Grace, MD

Daily, actually multiple times a day, we check the weather, winds, tides and currents using 4-5 different Apps. Also, discussions on the docks usually involve all things weather. On day two, we traveled a very long day in the rain across Long Island Sound to get ahead of the forecasted bad weather.  This enabled us to take advantage of small weather windows to keep moving south. This probably put us about two weeks ahead of folks who were only one day behind us.  We continue to hear reports of folks stuck between Port Washington and Atlantic Highlands due to impassable weather conditions. In our planning to leave Cape May, we once again saw one day to move or we would probably be stuck waiting for a weather shift.

Our route was cruising the Delaware Bay. This large, open, exposed body of water lies geographically Southeast to Northwest. The Bay is known for 2+currents and winds from the southeast or northwest create steep, short period, choppy sea. There is no place to run for cover along the Delaware Bay, so once you start the run you must finish it. We have cruised this stretch twice before and had Mother Nature on our side. This time, the winds are currents were going against us, but since they were both calm, we decide it would be a slow ride, using lots of extra gas, but a safe ride. Our planning and prep worked out, it was a long ride (about 90 minutes longer than the spring) but a smooth, safe ride.

We arrived in Chesapeake City, MD and the free wall had room so we took a spot and stayed two nights. This town does a great job with this free dock, you simply pay for electric and water, with the idea that you stop for the night and patronize the town. The Chesapeake and Delaware Canal (C and D Canal) is 14 miles long and connects the Chesapeake Bay with the Delaware River.  It is a ship canal intended to accommodate large ships and barges and thankfully during this trip we did not see or pass any. Chesapeake City is the only town in Maryland that is situated on this working commercial canal. It is a tiny town, population of about 750, but the historical downtown has cute shops and fun restaurants. We enjoyed touring an old bank that is now a jewelry and pottery shop. We walked around town with Linda and Jerry from Second Best and enjoyed new friends and drinks at The Tap Room and The Hole in the Wall.

Havre de Grace is a charming historic town known as “The Beautiful City by the Bay.” It is nestled where the Chesapeake Bay meets the Susquehanna River. Our cruise to this town was beautiful with great conditions and the current and wind giving us a great push. We actually saw 9 knots! Havre de Grace had plenty to do and we really loved this town. The five mile historical downtown is filled with antique shops, retro stores and fun, quirky boutiques. We popped into quite a few stores and enjoyed seeing memorabilia from our childhood and bought an old funky ring for $4.00. The Lafayette Trail was the first self guided narrated tour we have done and enjoyed learning and moving at our own pace. You download an app and follow a blue line in the streets, when you hit medallion in the sidewalk the app triggers and voices from the past tell you about the landmark. Havre de Grace encourages and supports a Public Art Plan and has over 24 pieces of art to stroll by and enjoy. At the entrance of our marina was the Market Street Brewery, where both nights we enjoyed beverages with Second Best and Calypso.

Chesapeake City, MD

The Hole in the Wall is an adorable little bar in a basement of a beautiful brick building that overlooks the canal. The name comes from a hole in the back of the bar where blacks would be served by reaching their hands in to receive a drink.

Havre de Grace (HdG), MD

Only one brewery in town, so we visited it nightly. My favorite Chocolate Covered Blackberry, a stout with blackberry. Got to enjoy lots of local talent during open mic night with Judi and Daz (Calypso) and Linda and Gerry (Second Best).
One stop on the Lafayette Trail, The Lock House Museum, which is on the Susquehanna and Tidewater Canal. We learned they used mules to pull the barges along the canal.
Concord Point Park and Lighthouse at the end of the wooden promenade.
Stopped in for dinner with Second Best and Calypso after reading rave reviews, the place was meh but company was superb.
Yes, Walmart delivers right to your boat!
Tidewater Marina was in a great location but had the tightest entry. We made it through with a little room to spare on each side.
  • Cape May, NJ to Chesapeake City, MD – September 25, 2023
    • Traveled the Delaware River to the C&D canal for 63.8 NM, cruising time 10 hours 30 minutes
    • Docked at Chesapeake City Town Docks at Government Wharf
  • Chesapeake City, MD to Havre da Grace, MD – September 27, 2023
    • Traveled the C&D Canal to the Chesapeake Bay to Susquehanna River for 20.5 NM cruising time 2hours 53 minutes
    • Docked at Tidewater Marina. Asked for a bulkhead spot for a side tide. The docks at Tidewater have very small finger piers. We could not get off with our dingy on the davits. Marina is nice but extremely narrow entrance and fairways.

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