Watershed Alley

Watershed Alley Watershed features the bounty of the Chesepeake watershed region: the Chester River, Chesapeake Bay,

07/12/2026
07/10/2026

Yellow Fin Tuna Crudo
Citrus Supremes, Bell Peppers, Pink Peppercorns, Avocado Oil, Tangerine Gel

Charred Octopus | Potato & Zucchini Latke, Green Beans, Olive Tapenade 🫶love your farms, love your food!💖 Watershed “BLT...
07/03/2026

Charred Octopus | Potato & Zucchini Latke, Green Beans, Olive Tapenade
đź«¶love your farms, love your food!đź’–

Watershed “BLT” Salad | Red Acres Hydroponics Mixed Lettuces, Marinated Cherry Tomatoes, Bacon Crumbles, Diced Age Provolone, Croutons, Green Goddess Dressing

Local Corn Panna Cotta | Maine Lobster, Green Tomato Consommé & Gel

Yellow Fin Tuna Crudo | Citrus Supremes, Bell Peppers, Pink Peppercorns, Avocado Oil, Tangerine Gel

07/03/2026

The Watershed Alley - Chestertown, Maryland. As we head into the weekend we are excited to be firing on all cylinders here at the Watershed. A beautiful summer menu; fresh ingredients, talented staff, what more could we ask for.

From the host stand: If you are thinking about coming in reservations are welcome, encouraged, and possibly a must. Jack, Kenny, and Flynn aka HIM are ready to find you a table for your watershed weekend.

From the Pass: in addition to Chefs killer menu we will be offering specials to be released come 5 o’clock.

A huge thank you to all of the birthdays, celebrations, and anniversaries we got to be apart of this past week. Sharing these moments are always the best times. Have yourself a watershed moment soon
Cheers to a great weekend 🍻🥂🎇
-James
Maître D’ & Farmer

Grilled Swordfish Sandwich - Red Acres Hydroponics Lettuce | Fried Green Tomato | Applewood Bacon | đź«¶love your farms, lo...
06/24/2026

Grilled Swordfish Sandwich - Red Acres Hydroponics Lettuce | Fried Green Tomato | Applewood Bacon | đź«¶love your farms, love your food!đź’– Tomato Jam | Garlic Aioli | Brioche Bread | THE BEST FRIES by Ryan Scruggs

This has been the winner for Lunch Service thus far. I ventured out of my comfort zone last week and tried this dish and was pleasantly surprised. I’m a chicken tender guy turned swordfish sandwich believer.

New lunch menu has been a big hit. Please join us Wednesday-Saturday for lunch or Tuesday for lunch for dinner. Reservations always welcomed for lunch service. Have a great week and come see us!

-James
Maître d’

Yellow Fin Tuna Crudo | Citrus Supremes, Bell Peppers, Pink Peppercorns, Avocado Oil, Tangerine GelOnly at the Watershed...
06/18/2026

Yellow Fin Tuna Crudo | Citrus Supremes, Bell Peppers, Pink Peppercorns, Avocado Oil, Tangerine Gel

Only at the Watershed Alley. Come enjoy a meal with us soon! Reservations are highly highly highly recommended.

- James

Local Rockfish Filet - Glazed Fennel, Mussels and Clams, Tomato-Pepper Coulis An absolute gem of a dish. Highly recommen...
06/17/2026

Local Rockfish Filet - Glazed Fennel, Mussels and Clams, Tomato-Pepper Coulis

An absolute gem of a dish. Highly recommended from me. Takes a lot for me to be impressed and yet this menu continues to wow me. Everything seems to be getting better and better. Hope to see you down the Alley.

Reservations are recommended

06/12/2026

As summer settles onto the Eastern Shore, some of the year’s most exciting ingredients are beginning to arrive in our kitchen.

Last evening, I had the opportunity to enjoy one of Chef Rodney and Chef Thomas’s newest creations—a beautifully prepared rockfish dish that perfectly captures the season. Fresh, thoughtful, and deeply rooted in the flavors of our region, it’s the kind of plate that reminds us why summer dining on the Shore is so special. It seems as though every year they find a new way for us to enjoy this beloved fish.

I am purposely on giving glimpses into this new menu because to truly appreciate the hard word and talent you must come in person.

At The Watershed, every dish begins with a commitment to local farms, local waters, and the talented people who bring these ingredients to life. From the produce harvested at Lockbriar Farms, Red Acres, as well as other local vendors to the seafood sourced from the Chesapeake, our menu is a reflection of the place we call home.

As the days grow longer and the dining rooms fill with friends, families, and celebrations, we’re grateful for everyone who chooses to spend an evening with us.

Summer reservations are filling quickly, and we would love to welcome you to the table. Reserve your seat today and experience the season at The Watershed.

From the host stand we have a few tables left for this weekend. I would not wait. You can make a reservation on Resy or by giving us a call. Flynn, Kenny, or Jack will be happy to accommodate you and yours.

Next week we have our Italian wine dinner. A beautiful menu and a thoughtful line up of wines. If interested you will need to book today.

Thank you to all of our guests for making the Watershed such a wonderful place of community.

James
Maître d’

06/11/2026

New menu this week! Come enjoy our summer offerings.

Hokkaido Scallops & Pork Belly W/  Broccoli Puree and Bok Choy, Shiitakes Mushrooms, and XO Sauce One of the best dishes...
05/14/2026

Hokkaido Scallops & Pork Belly
W/ Broccoli Puree and Bok Choy, Shiitakes Mushrooms, and XO Sauce

One of the best dishes I have ever had from . Beautifully plated, perfectly cooked. Worth ordering this weekend. We have tables available tonight for Pub Night + 1/2 priced bottles of wine.

Friday and Saturday filling up make your reservation today.

Special Sunday brunch also available. Don’t miss out on the fun opportunity.

Hope to see you down the Alley!
-James
Maître d’

Address

337 High Street
Chestertown, MD
21620

Opening Hours

Wednesday 5pm - 9pm
Thursday 5pm - 9pm
Friday 5pm - 9pm
Saturday 5pm - 9pm

Telephone

+14432829797

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