New Hot Spots and Things To Do in Chestertown

The summer is eclipsing us quickly, just as the moon eclipsed the sun recently. It is time to start thinking about the fall and all the goodness that this time of year brings. Plan a trip to our area and check out all the great new spots and things to do in Chestertown this fall!

Fridays in Chestertown – While Chestertown has its ever popular First Fridays (shops stay open late, offering adult beverages and snacks!), Rock Hall has also added Festive Friday to its roster of things to do in Chestertown. Similar to our First Friday, shops will stay open later and there will be live music of some sort every Friday on Main Street Rock Hall, in two locations (!) through October.

Local Festivals – The don’t-miss, late summer event, Chestertown’s very own Jazz Festival  is coming up in September, and of course Downrigging Weekend is at the end of October.

Shopping – If you are visiting us simply to relax and kick back — and perhaps you relax by shopping — then Chestertown fits the bill and you will surely find that perfect something you are searching for.  We try to keep you up to date with new places as they open up, as in this recent post. We’re excited to share a few more here. Check out what a variety we have:

  • Chestertown Electric is an interesting little shop… or perhaps museum is a better word?  All manner of vintage lighting and fans and other electronic items are for sale.  This is like mecca for the tinkerer.
  • Wye Upcycle is a treasure trove of shabby chic style painted furniture, home decor, lighting and more. A LOT of really cool things are in this shop.  And if you don’t see it except in your mind’s eye, the owner, Lisa, can probably make it for you.  🙂
  • A charming oasis of healing and relaxation only a mile from the inn…The Seed House offers yoga, open meditation, tea, coffee and juices, yummy snacks, and an herbal apothecary.  AND KOMBUCHA ON TAP!!!

And if all that shopping stokes your appetite, here’s a new restaurant to try:

  • Smoke, Rattle and Roll  got its start as a food truck.  Rolling around the state serving up BBQ sandwiches and platters, as well as nachos and tacos! Their brand new brick and mortar location is just 2 miles from the inn in Kent Plaza.  It’s a great addition to our already wonderful restaurant list.


So, come on down, up or over, and visit us! We promise you’ll find what you’re looking for, whatever it may be. There are lots of great new spots to check out and things to do in Chestertown this fall! While you are here, stay with us at our romantic bed and breakfast. We offer 7 luxurious rooms and 6 private cottages. Start planning your trip to Chestertown by booking online today!

Dine in Style! 

If you are looking for a unique dining experience, we have two amazing dining-series this season!

Check out Dining Under the Stars with Chef Kurt Peter starting May 2!


Gourmet Diner Club with chef Jordan Lloyd starting May 23!

Dining and entertainment experiences to remember! See our Specials page.

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