114 High
Your Home
Our Story
Luxury Stays
The Chestertown Life
Your Host, Katie
114 High
Your Home
Our Story
Luxury Stays
The Chestertown Life
Your Host, Katie
More
  • Your Home
  • Our Story
  • Luxury Stays
  • The Chestertown Life
  • Your Host, Katie
  • Your Home
  • Our Story
  • Luxury Stays
  • The Chestertown Life
  • Your Host, Katie

Experience Downtown Chestertown

Explore Chestertown

Dining

Dining

Dining

From upscale dining restaurants to authentic pizza joints, you won't be disappointed with the food here. Check out a list of some of our favorite spots to dine.

Our Reccomendations

Events

Dining

Dining

Check out our local events like the famous Chestertown Tea Party or the National Music Festival.

Event Calendar

Shopping

Shopping

Shopping

Downtown Chestertown features a range of shops from Fashionable apparel, fine jewelry, sportswear, collectibles and antiques, eclectic galleries, and so much more can be found. These independently-owned businesses not only create jobs and support our local economy, they are here to cater to customer’s individual needs.

Store Directory

Outdoors

Shopping

Shopping

From hiking to biking, our area boasts tons of opportunities to enjoy the great outdoors. Our favorite parks for hitting the trails are Eastern Neck Island Refuge and Sassafras NRMA

Our Dining Recommendations

Evergrain Bread Co.

Located just across the street from 114 High, this is our go-to for coffee, espresso, and incredible house made bread and pastries. You won't be disappointed when you start your day at Evergrain.


Our Menu Pick: Mini "Everknots" and an iced brown sugar latte

Evergrain Bread Co.

Bad Alfreds

Bad Alfred’s is a brewpub and distillery featuring house-made spirits, local craft beer and wood-fired pizzas. Just a short walk from 114 High. 


Our Menu Pick: The High Street Pizza

Bad Alfreds

Watershed Alley

A fine dining experience. The menua reflect the long-held commitment of Watershed Alley’s Chef to a combination of fresh ingredients, tasteful simplicity, and beautiful presentations - all inspired by the resources of the Chesapeake Bay watershed. Reservations recommended. 


Our Menu Pick: Any housemade dessert!


Watershed Alley

Luisa's Cucina Italiana

A Chestertown staple for over 20 years, Luisa's offers authentic Italian cuisine, wood-fired pizza, and something for everyone to enjoy. Luisa's is located uptown, in the Redner's shopping plaza.


Our Menu Picks: The Fancy Salad, Crab Dip, Tortellini Emiliani 

Luisa's Cucina Italiana

Modern Stone Age Kitchen

Scratch-made, industrial nut and seed-oil free artisan breads, pastries, delicious coffees and sandwiches.


Out Menu Picks:  Housemade Granola, Iced Vanilla Latte and Friday Night Pizzas!

Modern Stone Age Kitchen

Map of Downtown Chestertown

 Explore Chestertown’s rich history from 114 High. Walk to galleries, historic sites, and cultural gems that make every stay unforgettable.  Enjoy the slower pace of Chestertown. From river walks to coffee shops, 114 High offers access to laid-back local charm and natural beauty. 

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