A Local’s Guide to Chestertown This Fall (Beyond the Festivals)

Sep 23

Everyone knows about Chestertown’s iconic fall festivals — like Downrigging Weekend. But what do locals actually do?

If you’re thinking about moving to Kent County or simply want to explore Chestertown like a local this season, here’s your insider’s guide to all the cozy, quiet, and colorful ways to enjoy autumn — beyond the big events.

Best Spots for Fall Foliage & Walks

Wilmer Park: Right on the Chester River, perfect for morning strolls as the leaves change.
Gilchrest Rail Trail: A local favorite for biking or walking — with wide-open views and peaceful tree-lined paths.

Bring your camera or just your coffee — the views are unbeatable this time of year.

Chestertown’s Coziest Coffee & Lunch Spots

Fall is the perfect excuse to linger over coffee or a warm lunch. Check out these local favorites:

Evergrain Bread Co. – Best pastries and rustic breads around. Get there early.
Modern Stone Age Kitchen – Cozy, healthy, and great for a slower-paced lunch.
Stam’s Luncheonette – Retro charm meets small-town comfort food.

Bonus tip: Many of these shops double as work-from-home getaways or meeting spots — especially on crisp fall mornings.

Small Events & Local Markets

Skip the crowds and check out:

Chestertown Farmers Market (Saturdays) – Pumpkins, mums, cider, and artisan goods. They also offer a Wednesday market before Thanksgiving!
Local gallery pop-ups like Massoni Art are great to follow– Keep an eye out for artists hosting open studio events.
Brampton Inn hosts chef dinners, fireside pop-ups, and cozy fall events on their historic grounds
Crow Vineyard a local gem offering wine tastings, farm-to-table events, and scenic autumn views just outside Chestertown in Kennedyville

Scenic Drives & Bike Routes

There’s no better time to explore Kent County’s back roads. Try:

Quaker Neck Road to Cliffs City – Stunning fall foliage with Chester River views.
Worton to Betterton – Pass through farmland, quiet creeks, and tiny villages.
Rock Hall detour – A great sunset drive that ends near the water.

Bring your bike or take the car — either way, it’s peaceful and postcard-worthy.

Fall is Also a Great Time to Explore Real Estate

Here’s something most people don’t realize: fall is one of the best seasons to house hunt in Chestertown and the Eastern Shore. Fewer crowds, quieter neighborhoods, and homes framed in golden leaves make for peaceful showings.

Whether you’re looking for:

A waterfront retreat
A historic in-town property
A tucked-away cottage for weekend escapes

…this season offers a calm, beautiful backdrop to start your search.

Let’s Explore Chestertown Together

Whether you’re planning a quiet weekend or thinking about buying a home here, fall is the perfect time to connect with the community — and with someone who knows it inside and out.

Reach out today and let’s talk about your goals, your dream home, or just your favorite fall activity. And if you ever need crab cake recommendations, you know who to call!