Shopping Season in Chestertown, or: How to stay out of the malls!

Holiday season is upon us again, and like it or not, that means it’s also shopping season.  Whether it’s gifts, decor, food, or for donations, this is the time of year we all go out and spend our money. It’s important for that hard earned cash to get the most bang for each buck.  You want unique, possibly even one-of-a-kind gifts. Things that are heartfelt, and not “cookie-cutter” gifts

We have always encouraged folks to shop locally whenever possible.  Small mom and pop stores are usually the best place to find these unique and interesting things.

And if you’re visiting Chestertown, there are plenty of places to find the perfect gift (for others or yourself!). We have mentioned some of our favorites before here and here, and now we can add more to the list.

She She on High is a wonderful little store that’s more than a gift shop; you’ll find home goods  & decor as well as really cool furniture. And, yes, it’s on High Street.

Chris and Katie, the titular “she and she”, say that their painted distressed furniture is moving fast, as well as table ware, glasses, linens and paper products.  Planning a holiday party?  Might want to stop here and check out the wares.  This new shop, along with and Gabriel’s and Twigs and Teacups, will keep you out of the mall; we guarantee it.

Another new spot to visit is the collaborative gallery of fine art, craft, and design:  CREATE.  With 5 partner artists and an array of guest artists, this is a must visit! Textiles, art glass, jewelry, pottery, metal works, and more… tons of beautiful works that happen to make great gifts!  Add RiverArts and all the local artists‘ own studios, and you’re practically shopping in your own private atelier.

Late November into December, our area gets festive! Holiday concerts and house tours; art and antique fairs; and of course the parades!  First Friday in December (the 2nd), Chestertown looks like it’s straight out of a Frank Capra movie. The shops are open late, there are luminaries on the sidewalks, shopkeepers giving out hot cocoa, and someone in a Santa suit walking around town.  And not in an ironic way!   🙂

And of course, we have our own tiny gift shop if you want to take home a memento from your stay, or get a few last minute gifts without even going out.  Oh, and don’t forget the gift of an experience:  Gift Certificates to the inn are always a great idea!

I guess what we’re saying is, if you can’t find a great gift here in Chestertown, you won’t find it anywhere.

Avoid the mall.  Shop small.  Here in the land of pleasant living.


Brampton Inn Gift Certificates

Give the Gift of a Luxury Travel Experience!

Now thru December 31, 2021, when you buy a Brampton Inn Gift Certificate of $500 or more, you’ll receive a special code worth 10% off your next stay! Discount valid for stays thru December 31, 2022. Discount on room rate only, cannot be combined with other offers or third-party bookings. Not transferable. Must book direct at or call.

See Gift Certificate Information