Damian putting together our fold-up bikes on the dock in front of the Fish Whistle restaurant when we first arrived in Chestertown.

There’s no better way to explore a small waterfront town than on a bike, and since land transportation aboard a sailing vessel is hard to come by, we found “used but in good condition” fold-up bikes for half the price at a sailing thrift store called Bacon’s.  Join us as we motor up the narrowing Chester River and cycle around the town of Chestertown!

Location: Chester River

The Chester River is the faithful river on which we learned to sail three summers ago.  But we are familiar with the wide mouth of the river that wraps around Kent Narrows and then runs past Love Point and empties into the Chesapeake Bay.

The farther you follow from where the river comes from the more foreign our “old friend” looked like.  We motored out of the Corsica and followed the river further and further east.  The river narrowed and became more tame and shallow.  Her banks were lined with reeds and marsh.  The drastic change in the river’s appearance kept reminding me of the line from one of my favorite movies, The African Queen, in which Mr. Allnut tells Rosie that the Ulanga River takes on a completely different name when it changes appearance, and is called the Bora River.

Tricky Navigation

As the river narrowed, the deep middle got even more tricky to navigate, and we were forced to use our motor rather than sail tight tacks, running the risk of running aground in the shallow waters on either side.

Not quite Rosie from African Queen, but one captain’s wife at the helm as we motor up the Chester River toward Chestertown.  A motor boat races behind us in the distance.

We passed a few inlets of shallow water that had docks with fishing boats running out from small houses.  We passed a church camp at one bend of the river and passed an abandoned four story home or hotel or some sort of building that certainly had an interesting story behind it.

The foreboding remnant of a house or hotel that stands tall along the riverbanks of the Chester as she narrows.

Chestertown Marina, are you there?

As we approached the town of Chestertown, we were unclear about where the Chestertown Marina was located on the chart.  We passed one smaller marina that was filled mostly with motorboats on the starboard side and then a Yacht Club on the port side closer towards the town.  We decided to call the marina by phone but only got their voicemail.  Finally, as the town was rapidly coming upon us, we radioed the marina on the VHF:

Chestertown Marina, Chestertown Marina, Chestertown Marina.  This is the sailing vessel, Gem&I, over.”

The response?  About a minute and a half later was not what we had anticipated.

Gem&I, Gem&I, Gem&I.  This is the River Packet.  Switch to 7-2..”

The River Packet?  Who were they?  What did they have to do with hailing the marina in Chestertown.  Damian wasted no time in hesitation and quickly switched our VHF from 1-6 over to 7-2 pronto.

The River Packet told us that the Chestertown Marina was closed on Tuesdays, Wednesdays, and Thursdays–and it was a Thursday.  So there were three T-docks and the middle one was empty.  As long as we left before the marina opened again on Friday morning, we could tie up there for the night and get away without paying a dime!

Docking at Chestertown Marina

And that’s just what we did.  As we approached the marina and saw the three T-docks we had been told about, we discovered that the River Packet who had responded to our VHF hail was a large tourist riverboat that was tied up at the first of the three T-docks.  It was just sitting there waiting to entertain visiting tourists and show them the Chester River but looked bored as nobody appeared interested in taking her up on a riverboat cruise at the moment.  I guess we had given the skipper something to do that afternoon as he waited beside his VHF radio.


Saying No to Fish Whistle

The Chestertown Marina was situated around and in front of a restaurant called the Fish Whistle.  As soon as we approached, we smelled the seafood aromas wafting through the air and reminding us that the late lunchers were finishing their afternoon meals and that dinnertime was approaching.  But we are on a strict budget, and our “eat out” stipend was spent.  So what were we to do about our hungry stomachs and these delicious smells?

Make delicious food of our own, of course!  So once we had docked in the center T-dock, we used the left-overs and food supplies that we had onboard to have nachos and cheese and burritos!  We felt really good about this cost-effective decision.

Exploring on fold-up bikes

After our chow, we got ready to explore the town on our newly-purchased bikes.  For years, our sailing parents have touted about the uniqueness and bargains this sailing thrift store has to offer.  From PFDs to sail ties, this store has an assortment of marine supplies that are mostly used but a few still-in-the-package items.  Set in a warehouse in the middle of Annapolis, Bacon’s was friendly and helpful as Damian and I took a full afternoon one Monday to browse the various merchandise available that might be useful for our sailing needs and the needs of our boat.  We walked out of their with a boatswain’s chair, lightly used and of exceptional quality for $60 and both fold-up bikes for $95 each.  Still sticking with our tight budget, these were all items on our “wish list,” but with the exceptional prices, we were excited to make these items our own!

Look what we found at Bacon’s!

IMG_8958Our fold-up bikes fold in the middle, and we are able to bungee cord them to the sides of our boat on the stanchions.  Damian used his ratchet set to put them both together, and we were ready to explore the town named after our infamous river, the Chester.


Our bike tires were in desperate need for air.

Our Plan

  1. local post office (to mail some letters)
  2. gas station (to pump up bike tires)
  3. local library (to do some blogging and use the internet)
  4. grocery store (to pick up a few necessary grocery items)

Why not this street?

“I wouldn’t go on that street if I were you.  Go one more up,” shouted a man out of a pick up truck at Damian as we left the block the dock was on and headed up toward the town. The GPS had told us the route to take to the post office, and we were following it when we got the message that some of the streets in Chestertown were not necessarily ones we wanted to be traveling on, especially with being from out-of-town.

We followed the pick-up man’s advice and went up the main street passed little shops and restaurants to the town square that was adorned with a small park and fountain.  The Post Office was just beyond.  The mail attendant gave me directions to the local gas station, and with just a quarter, we were able to fill all four of our bike tires to make our rides much more enjoyable.  Then we were off the library!

Library Bike Parking

The alert that the town was not all that safe from our initial drive-by warning, we were leery of leaving our newly-bought bikes out front.  So Damian found a small alcove on the side of the library to prop our bikes in on the adjoining sidewalk, where we could keep an eye on them through the glass doors of the library.  So that is just what we did!

IMG_8953  After a few hours of blogging and doing a few internet-needed duties, we hopped on our bikes in pursuit of the local grocery store.  Damian had brought along his marine-issued backpack, and it was perfect to load up our groceries in for the bike ride back to the dock.

The ride home

On our bike ride home, we discovered a most-pleasing route through the little-known Washington College Campus.  The campus surprised us with brick, academic buildings, brick sidewalks, bright green lawns and shadowing trees who had seen more than a few decades.  Before long, we were back at the dock where Gem&I was tied, welcoming us home (as well as the sweet, meowing cries of our darling cat Booh-bah).

What a day it had been!

Gem&I on the T-dock at Chestertown Marina at sunset.

Have you been to Chestertown?  

Whether by boat or by car, have you been to Chestertown, MD?  What was your experience like?  Where did you visit and recommend?  Have you ever had success contacting Chestertown Marina by VHF?  What other marinas are in the area?  Share with us your thoughts; we would love to hear from you!