Chestertown Culinary Renaissance: Enter 98 Cannon Street with Joe Elliott


While opening dates remain far from confirmed, it is quite likely that over the next 18 months Chestertown will have four new restaurants in its historic district to call its own. After a few years of suffering the loss of several popular dining venues, including the beloved Brooks Tavern, Blue Heron, and the Lemon Leaf, a culinary renaissance is starting to take place.

The very first of this new wave will begin with the opening this spring of 98 Cannon Street, former home of the Fish Whistle and the Old Wharf restaurant, located at the town’s new marina.

As one might imagine, the Spy was beyond curious to this extraordinary explosion in culinary options. So much so that we tracked down the new owner 98 Cannon Street to understand what he and his team have planned for this iconic site on the banks of the Chester.

A financial advisor by profession, with a successful firm based in the Philadelphia area, Joe Elliott and his wife made the very deliberate decision to find a more rural environment for the couple and their three young daughters to gather on weekends. That’s what led him to Kent County a few years ago, but there was no desire to have any commercial interest in the town at all.

That started to change as Joe began to fall in love with his family’s new hometown. Going against a lifetime bias against owning businesses like restaurants, including his consistent advice to his clients to stay far away from these “opportunities,” Joe started to see a waterfront dining establishment as a personal challenge rather than a return on investment.

We caught up with Joe a few weeks ago at the Spy HQ to learn more.

This video is approximately four minutes in length. The new 98 Cannon Street design work is being done by M3 Architecture of Rock Hall


Letters to Editor

  1. Jamie Kirkpatrick says

    Very exciting, Joe! Love your energy, your vision, and your commitment to Chestertown. I hope the town and new tourists will support this venture; I know Kat and I will!

  2. Thad Bench says

    This interview shows an entrepreneur with his head in the game. I know that I have a lot of company wishing Joe and the rest of his team great success. This is a wonderful addition to our lovely town.

  3. I wish them nothing but best of luck crafting a venue worthy of its location.

  4. Looking forward to walking down to 98 Cannon Street, cracking crabs, and taking in the views of the River from the decks! Thanks for taking on this project you have our full support! Wishing you a speedy re-do and seemless opening! This is just what our little town needs!

  5. Chip Heaps says

    Joe that is wonderful news and we’re looking forward to dinner on the deck and having a spot we can enjoy by boat! Any idea on the timeline and I wish I had known about this when we broke bread a couple of months ago! 🙂

  6. At last, a crab deck for Chestertown…can’t wait. But, Joe, watch out for the wicked current in the river before you send inexperienced people out in kayaks 😙

  7. Maureen Ranville says

    Good luck with your endeavor. What a shame that the previous business owner, and Kent County native had to deal with years of loss of business due to all of the flooding before the new marina was built and the parking lot was fixed. What a shame that he was not able to bring any of his future visions for this location after the marina was improved. It’s great that we have new restaurants opening in Chestertown, but what a shame that a successful restaurant business has to relocate out of Chestertown and Kent County.

    • ann miller says

      I heartily concur. Odd that there was no mention in the article of the Fish Whistle as one of the several popular dining establishments leaving Chestertown. It really is to bad….
      Well – good luck to the new proprietors, we’ve long thought the area would be a great spot for a crab deck, as I gather from some of the other comments it is going to have.

      And good luck to the Fish Whistle at it’s new location in Cecil County/old Granary location.

  8. Carla Massoni says

    Thank you Joe!!! Can’t wait.

  9. Marty Stetson says

    The restaurant business is the number one business people go into but it is also the number one business that people fail. But thus sounds like it has been well thought out and if anyone is going to succeed in the restaurant business this should one. It will also add greatly to our new image of the waterfront of Chesterton and should help all the business in town to flourish. Looking forward to having my first meal there.

    • While taking a Kauffman Fasttrac business course at Chesapeake College several years ago I was able to access some interesting business information put together by the SCORE group. There were some important facts that provide some clue as to why many traditional restaurants fail in Kent County. The number of traditional “sit-down” restaurants per 1,000 residents FAR exceeds that of the rest of Maryland. Also, the number of part-time residents with vacation homes and the number of boat-slips in the County is surprisingly high. Armed with that knowledge it could be said that someone that’s willing to think out of the box a little and also aggressively market their “Brand” to part-time vacationers and boaters could do quite well. Hopefully the “new” marina will be a draw to boaters and the occasional “cruise” ship that will come to Chestertown. Good luck!

  10. Nick DiPasquale and Becky Robson says

    Go Joe, go! Although we are relatively new to Chestertown, we are year round permanent residents. We have always thought that Chestertown needs a decent restaurant on the water. One of our favorite places to eat and drink is The Bridges at Kent Narrows. Great food, good wine selection, wonderful view and music. Thanks for making this investment in the Chestertown community. Nick DiPasquale & Becky Robson

    • One note here:
      The Bridges at Kent Narrows probably benefits greatly by the bridge between Kent Island and Annapolis. Is that what it would take to make restaurants successful in Kent County 12 months of the year?

      Food for thought!

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