Everything You Need to Know About Chestertown First Friday

One of the most beloved traditions along the Eastern Shore of Maryland is Chestertown First Friday. Held on the first Friday of every month in historic downtown Chestertown, this is one event you won’t want to miss! Come stroll the streets, drop into the galleries and restaurants that stay open late, and sample wine and other goodies. Here’s how you can experience First Friday fun!

Chestertown First Friday is just one of many popular events you can attend along the Eastern Shore of Maryland.

About Chestertown First Friday

The beginning of a new month means the return of Chestertown First Friday! On every first Friday of the month, the local downtown merchants stay open late, welcoming visitors with open doors and warm smiles. Everyone is welcome to attend this free event and partake in the fun! Take your time browsing through the shops and art galleries, have a fabulous dinner out, and enjoy sips of wine here and there. 

Whether you’re on the hunt for a brand-new outfit, gifts for family and friends, or unique works of art, you can score some amazing deals at Chestertown First Friday. Many of the boutiques feature their newest products as well as recently discounted items. Likewise, the art galleries will have their newest and most impressive masterpieces on display. This event happens once a month, year-round, so you’ll have plenty of opportunities to attend!

Other Chestertown, MD, Events in 2019

Are you looking for more fun things to do during your stay in Chestertown? Mark your calendar for the following events and start making your plans to attend now!

Jigsaw Puzzle Contests at Brampton Inn:

If you’re a fan of Artifact Wooden Puzzles, you won’t want to miss our Jigsaw Puzzle Contest at Brampton Inn! The contest will be held on November 16, 2019, from 11 a.m. until 3 p.m. Book your stay, grab a friend, and put your skills to the test. The winners who finish first get a brand new Artifact puzzle!

Sultana Downrigging Weekend:

Known as one of the largest annual Tall Ship gatherings on the entire East Coast, you definitely won’t want to miss out on Sultana Downrigging Weekend! This highly-anticipated festival kicks off on Friday, November 1st and runs through the weekend. During the event, you’ll see the waterfront stock-full of ships, boats, and schooners of all sizes. In addition to musical performances and lectures, you’ll have plenty of opportunities to go sailing!

Chestertown Farmers Market:

Located in downtown’s beautiful Fountain Park, the Chestertown Farmers Market is the place to find fresh produce, herbs, bread, plants, soaps, and other goods. The market, which is open every Saturday from 8 a.m. until noon, runs until the last Saturday before Christmas. It will reopen again in March 2020.

Christmas in Chestertown:

There’s nothing more magical than Chestertown at Christmastime! Why not give the gift of experience this year, and treat your loved one to a holiday stay at Brampton Inn? A gift certificate to the Brampton is a thoughtful present for family members, friends, or business associates alike!

New Year’s Eve Party at Brampton Inn:

Celebrate December 31st in style at the Brampton! Instead of our usual afternoon tea, we will be hosting a New Year’s party from 6 until 7 p.m. Book your stay and join us for an elaborate appetizer buffet and champagne toast. Cheers!

Book Your Stay at Brampton Inn

When it comes to accommodations near Chestertown, MD, no place can compare to Brampton Inn. Our enchanting bed and breakfast offers the privacy and comfort you desire, and it’s just a stone’s throw from all the best shops, restaurants, and attractions downtown. After a fun-filled day, come relax in your elegant guest room or cottage. Many of our accommodations feature unique amenities such as wood-burning or gas fireplaces, en-suite bathrooms, and king or queen beds. Are you ready to experience your Eastern Shore of Maryland getaway to the fullest? Check our availability and book your stay today!

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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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