Shorter days. Longer nights. Cooler temperatures. Changing leaves. You know what that means: fall has officially arrived in Chestertown!

And with it comes one of the most important dates on the autumn calendar for anyone under four-feet tall or any grown-up with a sweet tooth and a penchant for dressing up: Halloween.

Luckily, Chestertown has no shortage of ways to celebrate the return of Spooky Season. So mark your calendars, grab your sweaters and Scooby Snacks, and get ready for a month full of treats, tricks, tall ships, and just a little bit of fright.

Downrigging Weekend: Tall Ships, Treats, and a Birthday Bash

What would Halloween in Chestertown be without a few tall ships on the horizon? Sultana’s Downrigging Weekend, the county’s largest annual public sail event, returns Oct. 30–Nov. 1 with a townwide celebration featuring everything from bluegrass to lectures. Whether you’re a maritime enthusiast or simply here for the festivities, there’s something for everyone.

This year is extra special: The schooner Sultana is turning 25! Join the birthday bash Friday night in the Music Village from 8:15 to 8:30 p.m. to sing “Happy Birthday” and raise a glass to the ship that helped make it all happen.

Once the birthday candles have been blown out (or the sails have been raised), stick around for the Halloween costume contest Saturday from 8 to 9 p.m. Who knows? You might just encounter a pirate or two.

Bringing little ghosts and goblins along for the ride? Sultana has you covered there, too. The Holt Center will open from 5 to 8 p.m. on Halloween to hand out treats to witches, zombies, and all manner of pint-sized creatures of the night.

The Chestertown Lions Club Halloween Parade: Candy, Costumes, and Community Spirit

If the promise of candy is enough to get your little monsters moving, don’t miss the Chestertown Lions Club Halloween Parade on Saturday, Oct. 31, from 1 to 3 p.m. along High Street.

This beloved local tradition promises plenty of costumes, merriment, and sweet treats. Come cheer on the parade, show off your own Halloween finery, and enjoy one of Chestertown’s favorite fall traditions. Just remember: You can never have too much candy. (Well, according to the kids, anyway.)

Historical Society Haunted Ghost Tours: Chestertown Has Spirits

Prefer your local history with a side of goosebumps? Good news: Chestertown has ghosts. (We knew those historic buildings were keeping a few secrets!)

The Historical Society of Kent County will host its Haunted Ghost Tours on Friday, Oct. 30, at 6:30, 7, and 7:30 p.m. A costumed guide, armed with a lantern and plenty of chilling tales, will lead visitors through the historic district’s spookiest spots.

Along the way, you’ll hear stories of murder, mayhem, and heartbreak from Chestertown’s past. It’s history class, but with considerably more ghosts—and considerably less homework.

Tickets are $20 per person, with up to two children admitted free per paying adult. Tickets are available here.

The Chestertown Artist Trail (CAT) Tour: A Different Kind of Hauntingly Good Art

Not everyone enjoys things that go bump in the night. If ghosts and ghouls aren’t your cup of pumpkin spice, check out the Chestertown Artist Trail (CAT) Tour during Downrigging Weekend, Oct. 30–Nov. 1.

This self-guided tour features more than 20 artists across 12 studios, offering a behind-the-scenes look at the creative talent that makes Chestertown special. From glass art and pottery to painting, fiber arts, and more, there’s plenty to discover.

No tricks here—just talented artisans, inspiring work, and perhaps the perfect one-of-a-kind treasure to take home. Consider it a Halloween treat for your inner art lover.

The Rocky Horror Show: Let’s Do the Time Warp Again!

Looking for a little theatrical mischief? The Garfield Center for the Arts at the Prince Theatre is serving up a Halloween-season classic with its production of The Rocky Horror Show, running through Halloween.

Come ready to do the Time Warp, cheer on local talent, and embrace the gloriously weird spirit of the season. We can’t promise the audience will toss toilet paper, but we can promise a lively show and a really good time.

Tickets are on sale here. Don’t dream it, be there!

Downtown Chestertown Association’s Scarecrow Contest: The Crows Have It

Last but certainly not least, keep an eye out for one of Chestertown’s quirkiest Halloween traditions: the Downtown Chestertown Association’s Scarecrow Decorating Contest.

These handmade characters pop up on posts, trees, and light poles throughout the historic district, bringing a little whimsy to the streets and plenty of smiles to passersby. Some are charming, some are downright silly, and a few might even make you do a double take.

Take a stroll downtown, see how many scarecrows you can spot, and pick your favorite. Just be warned: After seeing these creative characters, you may never look at a bale of hay the same way again.

A Little Magic, a Lot of Community

From haunted history and theatrical hijinks to tall ships, handmade scarecrows, and enough candy to keep the neighborhood dentists busy, Chestertown has plenty of ways to make Halloween memorable.

So dust off that costume, bundle up against the autumn chill, and get out to enjoy everything our charming waterfront town has to offer. Whether you’re chasing ghosts, chasing candy, or simply chasing the last bit of daylight, there’s a little Halloween magic waiting around every corner.

For a full account of what's going on in town, visit our community sourced Events Calendar. Happy haunting, Chestertown!