THINGS TO DO

In the area

EXPERIENCE A ONE-OF-A-KIND GETAWAY ON THE DELMARVA PENINSULA

Nestled along the peaceful Sassafras River, the Maryland Eastern Shore is brimming with unforgettable experiences. From scenic vineyards and charming small towns to river cruises and outdoor adventures, there’s something for every traveler to explore.

As part of the Chesapeake Wine Trail and the Chesapeake Country National Scenic Byway, this region offers breathtaking landscapes and vibrant local culture at every turn. Spend your days tasting award-winning wines, discovering unique shops and galleries, or enjoying water activities along the river.

After a full day of exploration, return to the Kitty Knight Inn—a cozy and elegant retreat where you can relax and recharge. Enjoy a delicious meal at our on-site restaurant, Deep Blue at Kitty Knight, featuring seasonal dishes and stunning views of the Sassafras River, perfect for unwinding before tomorrow’s adventures.

EASILY ACCESSIBLE FROM:

  • 15 minutes from Middletown, DE
  • 20 minutes from Chestertown, MD
  • 1 hour from Philadelphia via I-95
  • 1 hour from Annapolis, MD via US-301
  • Less than 2 hours from Baltimore, MD via I-95
  • Less than 2 hours from Washington, D.C. via US-301

Activities

MAKE THE MOST OF YOUR STAY ON THE SASSAFRAS

Sip & Savor Along the Chesapeake Wine Trail

Kitty Knight is proud to be on the Chesapeake Wine Trail, conveniently located near Broken Spoke Winery, Crow Vineyard and Winery. Our local vineyards offer tastings, as well as special events. Please view their websites for more information. Enjoy a glass or bottle of their fare while enjoying a Sassafras sunset in our restaurant, Deep Blue at Kitty Knight.

Discover Local Treasures & Unique Finds

Start your shopping adventure at the Kitty Knight gift shop, located on the first floor of the inn, where you'll find locally made arts and crafts, along with exclusive Deep Blue and Kitty Knight merchandise.


Just a short drive away, explore Arbor Georgetown, a beautifully curated boutique filled with stylish home accents and thoughtful gifts for every occasion. For fresh produce, locally grown flowers, and charming small gifts, don’t miss Cross Street Food & Garden—a favorite local stop.


Make time to visit Chestertown, a nearby historic town offering a variety of unique shops, galleries, and must-see boutiques. Or head to Rock Hall's Main Street, where you’ll uncover hidden gems—from coastal-inspired fashion to gourmet chocolates and one-of-a-kind keepsakes.

Set Sail on the Sassafras

No stay at the Kitty Knight Inn is complete without a scenic sunset cruise with Captain John’s Sassafras Adventures. Explore the beauty of the Sassafras River by boat, taking in peaceful views, local wildlife, and unforgettable sunsets.


Make your experience even more memorable by bringing along a takeout meal from our on-site restaurant, Deep Blue, perfect for enjoying on the water as you cruise in comfort and style.

Cast a Line on the Chesapeake

Whether you're a seasoned angler or trying something new, the Eastern Shore offers great fishing experiences just a short drive from the Kitty Knight Inn.


Learn the art of fly fishing with Chuck Jolly at Rosehill Farm, a beautifully preserved property on Mill Creek in Kent County. Practice your casting techniques on Chuck’s private pond in a peaceful, scenic setting. To book a session, call (410) 648-5334.


For those looking to explore the open waters, Elligail Charters in nearby Rock Hall offers premium fishing excursions and private charters on the Chesapeake Bay—perfect for a day of adventure and fresh catches.

Tee Off Near the Kitty Knight Inn

Golf enthusiasts will find a variety of exceptional courses just a short drive from the Kitty Knight Inn, offering scenic fairways and challenges for all skill levels.


Queenstown Harbor Golf (Queenstown, MD): Approximately 25 miles south, this premier golf destination features two waterfront courses—the River and the Lakes—set against the backdrop of the Chester River. It's renowned for its pristine conditions and top-tier amenities.


Back Creek Golf Club (Middletown, DE): Located about 20 miles north, this award-winning public course offers a links-style layout with generous fairways and challenging greens, suitable for golfers of all levels.


Frog Hollow Golf Club (Middletown, DE): Also around 20 miles away, Frog Hollow provides a well-maintained, links-style 18-hole championship course that is both challenging and player-friendly.


Chester River Yacht & Country Club (Chestertown, MD): Just 15 miles southwest, this private club offers a picturesque 18-hole course along the Chester River, combining challenging play with stunning views. Please note that access may be limited to members or guests.


Whether you're looking to play a casual round or seeking a more competitive game, these nearby courses provide excellent options to enhance your stay at the Kitty Knight Inn.