All You Need to Know About the Chestertown, MD, Tea Party Festival and Memorial Day Parade

Memorial Day Weekend is one of the most popular weekends of the year, and for good reason! The sun is out, the air is warm, and everyone is ready to welcome the arrival of summer. Memorial Day Weekend in our historic town is no exception! There’s no better place to go for a 3-day getaway. When you’re in town for the holiday, be sure to check out the Chestertown, MD, Tea Party Festival and Memorial Day Parade! Below, we’ve listed everything you need to know about it. Don’t forget to request our free Travel Guide to the Eastern Shore of Maryland for more of our best local recommendations!

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What You Need to Know about the Chestertown, MD, Tea Party Festival and Memorial Day Parade

One of historic Chestertown’s most iconic events is the Tea Party Festival! This fun occasion has been a staple in the community since 1976! What began as a symbolic act of rebellion has transformed into a festive, weekend-long tradition that signals the beginning of summer. Keep reading to learn more!

The Chestertown Tea Party: A Piece of Maryland History

The Tea Party Festival commemorates a colonial-era protest against British excise duties. This protest took place in 1774 as a response to the British Tea Act. It resulted in the takeover of a British brigantine anchored in the Chester River. Disgruntled Chestertown residents took the ship’s cargo—loads of British tea—and threw it into the river. Today, the event is more celebratory and educational than rebellious in nature!

About the Tea Party Festival

2019 Dates: Friday, May 24—Sunday, May 26

We highly recommend coming in your colonial garb and joining in on the fun! The grand parade is one of the most popular summer events in Chestertown, but there are plenty of other exciting events. Be sure to explore the complete Tea Party Festival lineup and enjoy running races, beer and wine tasting, and, of course, watching the famous reenactment of the Tea Party itself! Delicious food is available all weekend—we especially recommend visiting with the Lyons and Rotary clubs for some delicious barbecue and crab cakes. The best part? The funds raised benefit local charities!

In addition to plenty of tasty treats, check out the Chester River Chorale performance and the wide variety of artisan vendors. You may even see Benjamin Franklin walking the streets of Chestertown!

Chestertown Tea Party Reenactment Information

The reenactment of the historic Chestertown Tea Party is the centerpiece of the festival! It takes place annually on the Saturday of Memorial Day Weekend at 2:00 p.m. If you have time for only one Tea Party Festival event, make it this one! The reenactment is held along the Chester River in historic downtown Chestertown.

Parade Information

The Chestertown Memorial Day Parade is a fantastic example of our town’s laid-back charm and friendly community. You won’t find anything like it in Baltimore or D.C.! Plan to attend the parade this year, which always features veterans, firefighters, antique vehicles, and the ever-fabulous Kent County Community Marching Band. In the past, the Budweiser Clydesdales have even made an appearance! The parade begins on Saturday at 10 a.m. by Dixon Valve and Coupling Co.

Spend This Memorial Day Weekend at Brampton Inn!Sunset Cottage at Brampton Inn

After you turn back the clock and share in the fun of Chestertown Tea Party Weekend, you’ll need a comfortable, spacious, and welcoming place to rest and relax. There’s no better place to do just that than Brampton Inn! Here, our guests are treated like family. Our bright and beautiful rooms and cottages offer respite from the hustle and bustle. Here, you can sit back, relax, and “porch surf” with us (trust us…it’s a thing)! In the morning, wake up to fresh, country air and our homemade, gourmet breakfast. Then, in the afternoon, join us for Tea Time and Social Hour! Throughout the year, Brampton Inn also hosts a variety of festive on-site events. Isn’t it time you came to experience them for yourself?

You won’t want to miss the Chestertown, MD, Tea Party Festival and Memorial Day Parade this year. Book a stay with us now so you can start looking forward to the advent of summer!