Our First Night on Anchor With an On-the Water Eastport Oyster Boys Concert

June, 2021:

“Ubiquitous!” we heard while dinghying by.  Phillip’s head snapped around.  I did a visual sweep of the mooring field.  It was the first time anyone had shouted our boat’s name at us and I think it baffled us more than anything, like how did they know?  But, once we saw a hand waving off the transom of a beautiful blue Sabre, it clicked.  We’re being summoned my surprised face said to Phillip. 

“Ahoy!” a chipper sailor said to us as we dinghied up to s/v Talisman to meet the eager and enthusiastic duo: Jeff and Ginger.  We also learned something that has been often reenforced during our summer aboard UbiQ: there are many sailors out there who are “looking for an Outbound.”  Turns out, the Outbound 46 is even more coveted than we had known.  Jeff had been looking at them for several years, scouring Yachtworld listings for the rare gem that emerged there, even toying with the idea of perhaps getting on the list for a new build.  Needless to say, he was really excited when he found a fairly new Outbound 46 had moored just a few balls over from him in the main mooring field in Spa Creek near downtown Annapolis.  As we bobbed next to their boat, Jeff and Ginger peppered us with questions, wanting to know when we had purchased our Outbound, what we thought of the boat, what type of sailing we had done so far, how she performed, did we like living aboard her, etc.  Phillip and I were happy to answer.  Who doesn’t love talking about their beautiful boat, right?  Makes all those hours wiping worth it. 

Jeff and Ginger told us a bit about their boat, a 38-foot (if I recall correctly) Sabre.  A gorgeous boat.  And, it didn’t surprise us as we’ve found many Sabre owners are drawn to the Outbound.  Our former owner, Jim, definitely was.  Must be something about the build quality, performance, or design that just speaks to Sabre sailors.  Jeff and Ginger had been sailing their Sabre around the Chesapeake and east coast for many years.  In that regard, it was a fortuitous meeting as they wanted to know more about our Outbound, and we wanted to know more about all the local anchorages.  And, looking back, I think it was really Phillip and I who truly took the most valuable knowledge away from that chance rendezvous, because Jeff and Ginger opened the door for one of the most magical nights we have spent on the hook.  And, it turned out to be our very first on UbiQ, which made it even better and infinitely more memorable. 

“To St. Michaels, on Sunday,” we told Jeff when he asked where we were headed next.  Over the summer months, Phillip and I had been getting the boat dialed in, knocking out some small projects with our former owner Jim, and prepping the boat for this little jaunt around the Chesapeake.  It was finally time for us to “go cruising” on the new boat!  Many local sailors had recommended St. Michaels to us as it was a nice day-sail from Annapolis across the Chesapeake to the east shore, up the Eastern Bay and promised a charming walk-about downtown with a few lovely restaurants and bars and an exceptional maritime museum.  Phillip and I were both super excited to finally start doing what we bought this amazing boat for!  To GO!  But, Jeff had a suggestion for us.    

“Let me give you a tip,” Jeff said with sly smile.  “Leave Saturday,” he paused.  Our eyebrows raised.  “St. Michaels will be there.  Postpone it for a day and anchor one night in West River.” 

Why would Jeff recommend we postpone St. Michaels?  To experience the (self-proclaimed) Musical Goodwill Ambassadors of the Chesapeake!  The EASTPORT OYSTER BOYS!  Have any of you heard of this incredible little home-grown Chesapeake band?  We had no idea what we were in for but, damn, what a treat! 

Unbeknownst to us, the scuttlebutt all over Eastport was that the Oyster Boys were planning on having one final on-the-water concert before their trombone player, Andy, was rumored to be leaving the band to finally start his cruising chapter.  And, where was this infamous finale going to take place?  In the West River where the local Sabre owners were also hosting a Sabre round-up.  When?  On Saturday night!  That’s why Jeff recommended we leave a day early for our planned St. Michaels trip so we could drop the hook for one night first in West River to be sure we did not miss this rare on-the-water treat! 

Phillip and I had never been to West River.  We hadn’t been anywhere other than Annapolis, really, in the Chesapeake.  We had also never been to a dinghy-up on-the-water concert.  Jeff was right.  St. Michaels would be there.  It was an easy decision for us.  Phillip and I decided to leave the main mooring field on Saturday just as Jeff had recommended.  We enjoyed an exceptional sail down the Chesapeake, and actually found ourselves in not one, but three different regattas along the way.  Regattas seem to rustle up every day in Annapolis, and this day was no exception. 

After a fantastic brisk sail down, we poked our way into West River, saw the Sabre round-up further up the river, but decided to drop a good ways back in a little nook that looked perfect for us.  We laid out 100 feet of chain (enough to make us feel comfy) snubbed her up, and *voila* there she was.  UbiQ finally floating happily on her hook.  Phillip and I breathed a collective Ahhhh … This was it.  Everything we had been working so hard for since December of the year prior.  Boat shopping, negotiating, getting financing, getting our old boat sold, flying back and forth to Annapolis several times.  Turning our somewhat settled life upside down basically.  All to land right where we had, aboard a gorgeous boat, a premier ocean cruiser—our Outbound 46—floating happily on her hook.  The moment was so perfect … we left! 

We had shore to explore, people!  We love our boat, that’s for sure, but there’s another reason we cruise – to travel!  Set foot in new cities and ports.  See new sights.  Eat everything we see!  It was time to explore.  And, the minute we started to dinghy up, we knew this great spinning world was sending us an omen.  The first bar we came to during our first night on the hook was like a warm welcome hug from home: Pirates Cove.  Sure, I’ll bet there are no less than a thousand worn-down driftwood-and-tiki-hut-looking Pirate’s Cove bars all over the world.  But, the fact that we found one right there, where we had come on a whim told us (like the sight of dolphins always do) We’re doing something right here. 

So, what did we do?  Bellied up to the bar, of course, and tried our first ever round of piping hot Old Bay dusted wings!  Washed down with two margaritas … naturally.  Two apiece that is … naturally. 

Then, we dinghied back out into West River where the pings and toots of tuning instruments drew us in.  A crowd was starting to form around the power boat in the center and I had the privilege of first laying my eyes on the Eastport Oyster Boys band. 

UbiQ’s former owners, Jim and Ann, had told us a good deal about them, as they had had the privilege of taking in several EOB on-the-water concerts, but nothing could truly prepare us for the treat of a live, sun-down serenade.  There was a sax player, a tambourine, a trombone, drums, a trumpet, even a tuba!  All on the foredeck of a power boat playing New Orleans-esque funk for all who were willing to dinghy up and dance a little.  But, don’t let my words do it any injustice, listen for yourself! 

The Eastport Oyster Boys were a real treat!  And something Phillip and I would have never had the privilege of seeing (and hearing) had it not been for fellow cruisers and our stand-out boat.  Many thanks to Jeff and Ginger aboard s/v Talisman for this awesome tip and invite!  Phillip and I had an amazing time.  We ended up being one of the few dinghies who had a dinghy anchor (thank you Mantus!) so we actually ended up being the center of the redneck yacht club for most of the evening, which was quite ironic (as it was our first time at an EOB concert) but really fun at the same time! 

I’m sure UbiQ got a great chuckle out of us as we dinghied back to her after the concert dispersed, whispering remnants of our enchanting little backwater, salty band experience.  I know, I know, she said to us, this is not my first Oyster Boys concert, reminding us again as the sun melted to a stunning pink and blue behind her, Ubiquitous has so much to share with us. 

4 thoughts on “Our First Night on Anchor With an On-the Water Eastport Oyster Boys Concert

  • Hi, what does your Outbound draw? We have a 2006 Outbound 44 and she draws 6’7”. My partner has already done years of Caribbean cruising and we are wondering where we could take her in Bahamas and Atlantic coastal cruising without too much stress about running aground or going under bridges. Don’t want to always be white knuckling it with the tides.

    • Hi there! Sorry I did not get back to you sooner on this. We were planning our jump across to the Bahamas and wifi became scarce. But, that will tell you … it’s not difficult at all to do the Bahamas in our Outbound 46, but we only draw 5’6″. We’re the shoal draft version. They make a longer keeled version that is, as you mention 6’7″. While that definitely does NOT rule out the Bahamas or the Caribbean (we have met many 7-foot keelers who do both) you just have to be more aware of your depth more often and play the tides more. But, the shorter, 5’6″ draft on our Outbound 46 was definitely a draw for us as that was roughly equivalent to our old boat (5’2″, technically) but we treat both as “six feet” for comfort and that has served us well. We also have a 63-foot mast. Not ideal for many ICW bridges, but we usually prefer to go on the outside anyway as we find offshore trips are more enjoyable and less risky (depending on weather, traffic, fog, logs, bridges, etc.) than inner-coastal ICW trips. Hope that helps. Happy cruising!

  • Hey guys. What a super story. Annie, keep writing you’re getting better with each post. Best things to show up in my in box. Thanks.

    West River story. In my J28 days. Anchored there one afternoon since a local sailor had said it was a nice cruise from our new-to-us berth in Back Creek. Hook down and settling in to enjoy the scenery. In comes another small sloop, She’s on the bow and he’s steering. She gets the anchor ready and calls out loudly, “Where?” He says, “Farther in.” She says, “No.” Bump! Anchor flies off the bow roller and she hollers something akin to Ooops. Anyway, they anchored and we waved. Some time later I met the couple who were as new to the area as I was and we had a good laugh.

    My daughter bought a Sabre 30 and loves it. Mama and I went to look at my idea of THE perfect boat to which she said she’d prefer a Sabre. Oh well. Marital harmony.

    Keep well,
    Cape Cod

    • Ha ha! That’s a great story. Sometimes “oops” is the best place to anchor. If the anchor knows … So glad you have so many memorable memories from this area as well, Norm. We have been loving the Chesapeake. Great times to be had here for sure, and we only explored a fraction (of a fraction) of what it has to offer.

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