So Many Festivals! So Much Fun in Chestertown!

When spring turns to summer things kick into high gear here on the Eastern Shore:

The warm weather brings EVERYONE out onto the sidewalks during First Fridays. (And now we have 3rd Thursdays to look forward to as well).  Restaurants with al fresco dining instantly increase their seating capacity.  The farmers market is jam packed each Saturday.

And just like in the fall,  there is a festival of some sort practically every weekend.   Some of our favorites include  Paint the Town , from April 28 to May 1st when the whole town is filled with plein air artists painting or drawing in public: you can watch a work of art come to fruition and then bid on it only a day later!

There’s also Porchfest on the afternoon of May 14, when musicians are playing live on porches throughout downtown Chestertown,  creating a progressive music festival to enjoy in between stops at galleries and shops.  Many cities across the country have been doing this for a few years, but I would bet good money that Chestertown has more porches per square mile than most!

Of course the big momma of festivals is on Memorial Day weekend May 27-29 when Chestertown celebrates its revolutionary history with the Tea Party Festival.  A street party on Friday night and a town wide party all day Saturday.  More fun with a crazy raft race on Sunday. So much to do and see.

BUT, quickly becoming another of one our favorites is the  National Music Festival.  For two weeks in June (this year it’s the 5th through 18th),  Chestertown becomes a living and breathing orchestral training ground.  For classical music enthusiasts, this is THE time to visit the Eastern Shore.   More than 100 gifted apprentices and about 30 mentors; over 200 open and free rehearsals and more than 30 performances, many of them free. Read some of our thoughts from previous years here and here.

It’s quite a boon to have so many opportunities for entertainment in this tiny, rural county. From blues and jazz to bluegrass and classical, we have nearly all genres covered.

Yet another perk from the Land of Pleasant Living.  Come join us, won’t you?

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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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