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Things To Do

Johnny and I took some time to explore this quaint little town and we're so excited to share a few of our favorite spots with you! :)
Modern Stone Age Kitchen

Modern Stone Age Kitchen

236 Cannon Street, Chestertown, MD 21620

An award winning kitchen where everything is prepared 100% from scratch (bread, pizza, cheese, tacos, soups, sandwiches and even cookies). They also offer fun cooking classes that you can sign up for in advance!

Watershed Alley

Watershed Alley

337 High Street, Chestertown, MD 21620

A local favorite! Serves dishes that are authentic to the Chesapeake origins.

Karma Cleanse Cafe

Karma Cleanse Cafe

860 High Street, Chestertown, MD 21620

A healthy plant based cafe with salads, acai bowls, juices, smoothies and energy treats!

The Kitchen and the Pub at the Imperial

The Kitchen and the Pub at the Imperial

208 High Street, Chestertown, MD 21620

The Kitchen at The Imperial menu changes frequently based on the availability of fresh, local ingredients. They offer brunch, lunch, and dinner.

BAD Alfred's Distilling

BAD Alfred's Distilling

323 High Street, Chestertown, MD 21620

Bad Alfred’s is a brewpub and distillery featuring house-made spirits, local craft beer and wood-fired pizzas. We loved the pizza.

Figg's Ordinary

Figg's Ordinary

207 South Cross Street, Chestertown, MD 21620

Figg’s is a Gluten Free facility. You can sit down to eat or grab and go!

Casa Carmen Wines

Casa Carmen Wines

312 Cannon Street, Chestertown, MD 21620
Radcliffe Yoga Studio

Radcliffe Yoga Studio

860 High Street, Chestertown, MD 21620

Only $15 for an hour yoga class! They offer a wide range of classes and the studio is a little dream!

Walnut & Wool

Walnut & Wool

321 High Street, Chestertown, MD 21620

Walnut & Wool has become known for mixing vintage & new. They specialize in painted furniture, women's/mens clothing, funky vintage decor, and handmade gifts. It gave us free people and anthropologie vibes. Johnny also bought a cool shirt there!