Top Four Romantic Eastern Shore Adventures to Enjoy This Winter - Koch Homes

Top Four Romantic Eastern Shore Adventures to Enjoy This Winter

Uncategorized l February 13, 2023

Maryland is known for its romantic Eastern Shore adventures this time of year. Nestled on the famous Chesapeake Bay and with easy access to the Atlantic Ocean, Maryland’s Eastern Shore boasts timeless landmarks and activities to suit any visitor.

Below, we’ll share four amazing romantic Eastern Shore adventures to consider for your winter or Valentine’s Day getaway. Discover the richness and charm of Maryland’s beloved coast that make it a top destination for many.

Four Romantic Eastern Shore Adventures Perfect for Winter Celebrations


St. Michaels

Enjoy the cool and calm waters at St. Michaels. Take a boat tour on the Selina II and travel back in time, embarking on a moonlight sail with wine tasting and great food. These tours offer a private charter that can accommodate even a group of friends.

Consider a historic excursion at the Hooper Strait Lighthouse. Built in the late 1800s, it now stands on Navy Point. It’s full of intriguing maritime artifacts and objects that illustrate stories of life during that time.


Arrange a romantic stay on Oxford’s waterfront. Here, you’ll discover charming small towns lined with trees and brick sidewalks. For a relaxing, quiet holiday in a photo-worthy environment, this is the place.

Take a stroll along quaint houses and shops, and visit nature trails and shimmering waterfronts. Stay at the Robert Morris Inn, built in the 1700s. It has colonial details such as wood floors and beams, brick walls and stone mantels. Dine in and enjoy the inn’s famous fish and chips and oyster pot pie.


Retreat to a time of simplicity and natural charm in Chestertown. A historic place, this town offers picturesque views along the Chester River.

Established in the early 1700s, Chestertown is a historic college site with brick sidewalks, small shops, inns and restaurants to explore while you’re there. If you love Colonial-style buildings, you’ll settle well in this place.


Easton, Maryland offers big time luxury with a small town charm — Full of remarkable adventure where you can savor delicious dining, peruse local shops, admire beautiful art galleries, and make this Valentine’s Day truly memorable.

Explore the rich history in one of America’s oldest churches, marvel at the beauty the Academy Art Museum delivers, find wonderful entertainment at the Avalon Theatre, or spend a romantic moment walking or riding throughout some of the 400 acres of protected forests, wetlands, and wildlife.

How to Enjoy The Eastern Shore This Season and Beyond

Romantic Eastern Shore adventures are waiting for you in Maryland. There’s so much to enjoy that one day on the Eastern Shore is not enough to take advantage of all its amenities! 

Koch Homes, a home builder known for our presence in charming Eastern Shore communities, delivers single-family homes in great locations such as Bretridge. Located on the Eastern Shore, this established community has new Koch homes with immersive open layouts, impressive finishing touches and luxury details. 

Contact us today to claim our final remaining home here and enjoy Eastern Shore adventures with ease.