There is an endless amount to experience on the Eastern Shore. Use our guides as your curated list for the best restaurant recs, family-friendly activities, and VIP experiences in the area! We’ve spent years investigating the area to bring you activity ideas for every age and every type of vacationer.
Golf at the Links at Perry Cabin
Staying at a Tremezzo Property grants you the opportunity for sponsored play at this iconic and exclusive luxury club. Reach out to us if you desire a tee time!
INN AT PERRY CABIN
The Premiere Luxury Resort on the Eastern Shore. Relax solo or as a couple at the spa - or get exclusive access to the world-renowned Links at Perry Cabin with your Tremezzo Stay.
Eastern shore brewing
This kid-friendly spot is one of our favorites with award-winning beers, outdoor seating, and that classic old-world Eastern Shore feel.
St. Michael’s Winery
Who doesn’t love a good wine tasting? With over 18 wines in their cellar, they’ve got something for every pallet. Try a few, grab a couple bottles, and let us know your favorites!
Lyon Rum | Windon Distilling
Prefer something a bit stronger? Why not try a rum tasting along the Eastern Shore! Named Best Craft Rum Distillery in the annual USA TODAY 10 Best contest in both 2021 & 2020!
BIke Tours
There are some fantastic bike tours of the Eastern Shore! This helpful guide can be easily downloaded to your phone and/or printed. It includes where to rent bikes, iconic tours, and Maryland rules of the road!
Chesapeake Bay Maritime Museum
This family-friendly museum campus offers everything from a historic shore-side lighthouse (1879 Hooper Strait Lighthouse) to interactive exhibits (wanna teach the kids how to shuck an oyster?), to interpretive gardens and a living shoreline. Experience the history, culture, and charm of the entire Chesapeake Bay region firsthand!
Antiquing
There is no shortage of historic treasure shops along the Eastern Shore! Here are some of our favorites:
Saint Michaels Farmers Market
This is the Eastern Shore’s small-town, producer-only market. On Saturday mornings from April through November, grab a tote bag and bring your family for fresh food and a fabulous local community experience!
Saint Michaels Museum & Historical Walking Tour
Tourists and residents alike enjoy the Museum for its vivid interpretation of St. Michaels’ history and culture, represented by historic artifacts and oral histories of the people. There is a continuing calendar of dynamic programs and activities for adults and children, plus guided and self-guided walking tours of this iconic village.
Classic Motor Museum
The Classic Motor Museum (CMM) is dedicated to appreciating and preserving America’s heritage of automotive innovation and adaptation. This family-friendly museum boasts something for everyone! They also host a ‘cars and coffee’ gathering in the summer on Saturdays at 9 AM.
The Oxford Museum
Day trip to historic Oxford by ferry! This historic town boasts an audio walking tour with over 30 stops and a museum with exhibits exclusively devoted to its people, their way of life, and their contribution to our country since the 1600s.
Sail & Cruise along the Chesapeake
Private charters, sunset sails and more await you on these sightseeing adventures along the Chesapeake. Here are some of our favorite companies:
Festival Fun
Enjoy a good festival? St Michaels has world-renowned celebrations all along the Chesapeake. From wine to oysters, there’s a theme for everyone.
Sugar & Toys
Score some homemade ice cream at one of the local old-fashioned Ice Cream Parlours, or load up the kids with local confections (including some vegan delights) and gifts at Old Town Candy Co.
Tilghman Island
Spend the day in Tilghman Island. There is so much to do in this quaint fisherman’s town, from renting a powerboat or pontoon to watch the sunset along the water to grabbiing a bike or kayak and exploring the area!