Fall has arrived on Maryland’s Eastern Shore! Join us as we delve into this fresh, crisp season in quaint Chesapeake Bay towns that contain a collage of charming churches, manicured federal, colonial and Victorian homes, historic maritime heritage, diverse artistic talents, and pleasant southern culture.
Our Fall exploration will include the relaxed, sleepy bay towns of St. Michaels, Oxford, Easton, and Chestertown where each day begins with a peaceful, glorious view and ends at night in candlelight elegance. In the next four days, we will toast in the Fall-time happiness at several quaint towns, discover interesting maritime history, marvel at pristine antique cars, run from ghosts and cruise the night away!
Day One: Lunch in Historic Centreville
Our drive to Maryland will be dazzled with colorful trees lining our way. Once we arrive in the picturesque, historic town of Centreville, we will enjoy an included lunch and have time to take in the charming surroundings while wandering the brick lined sidewalks.
Day One: Tidewater Inn
Then it’s time to get comfortable in our historic accommodations at the Tidewater Inn in the lovely town of Easton before going out on the town at your leisure for dinner on your own to enjoy the tastes of the Eastern Shore.
Day Two: Oxford Museum & Walk
This morning, we’ll be entranced by the charming, tranquil town of Oxford. A tour of the Oxford Museum will teach us of the 350 years of colonial and American history that led the town from being one of the country’s earliest ports to the present as a premier sailing destination.
Next, long time local Leo will guide us on an unforgettable walking tour with stories only a native can share. Afterwards, we may even extend the tour for a drink with Leo at our home, the Robert Morris Inn!
Day Two: Lunch in Easton
The Culture Capitol of the Eastern Shore is next on our list. We’ll spend the afternoon exploring Easton, the idyllic, small town that is home to award winning restaurants, eclectic art galleries, and fine boutiques.
You’ll be sure to find a wonderful restaurant among the downtown to have a memorable lunch on our own.
Day Two: Chestertown & Dinner Cruise
We will have time to wander and browse the historic tree lined streets of Chestertown before our evening dinner cruise where we will enjoy the beautiful scenery and catch a spectacular sunset over the banks of the Chester River.
Day Three: Chesapeake Bay Maritime Museum
Today we have the pleasure of visiting the idyllic waterfront village of St. Michaels, historically known as “the town that fooled the British”. You’ll be immediately taken by its charm and historical feel as you wander the randomly patterned brick sidewalks that take you past homes dating back to the mid-1600.
We’ll start at the Chesapeake Bay Maritime Museum. Here, we’ll discover the peace and solitude of the bay, take in the beautiful changing exhibitions in the Steamboat Building, climb the historic 1879 Hooper Strait Lighthouse for magnificent views, learn about the heritage of oystering, water fowling, and much more!
Day Three: Downtown St. Michaels
Classic Motor Museum
Now take the afternoon to wander this lovely town, shop boutiques, browse antiques, and find your inner artist at the numerous galleries. Indulge in the gifts of the Chesapeake Bay for lunch on your own and don’t miss the homemade ice cream on Talbot Street.
Later in the afternoon, we’ll be taken back in time at the Classic Motor Museum in St. Michaels that houses pristine examples of pre- and post-WWII classic automobiles, mid-century muscle cars, vintage trucks, motorcycles, and other era inspired collectibles
Day Three: Dinner & Ghost Walk
After dinner on your own in town, you will have the option of walking the ghostly path of rowdy women who get about town at night on a St. Michaels Ghost Walk or heading back to the Robert Morris Inn to relax after a day filled with maritime charm.
Day Four: Sinking Springs Herb Farm Lunch
An extra special treat awaits us on our way back towards New Jersey; an exclusive retreat on a scenic 130-acre farm at historic Bristoll Plantation. Here at historic Sinking Springs Herb Farm we will enjoy a delicious lunch in a rural setting featuring an 18th century provincial plantation log house, a rustic barn with a bright airy loft, delightful aromatic gardens, and a private pond with an island.
There will be time to stroll and explore the grounds, including the amazing 442-year-old sycamore tree born in 1578 and connect with nature though creation of a thyme craft. A wonderful way to end a spectacular Fall getaway!
Pricing & Departures:
Departs from Ridgewood’s Graydon Pool parking lot (corner of Linwood Avenue & Northern Parkway) at 7:15 AM and returns at approximately 5:30 PM
Departs the Chatham Middle School at 480 Main Street (behind the Methodist Church) at 8:00 AM and returns at approximately 4:45 PM
Departs from South Plainfield High School at the end of Lane Avenue at 8:45 AM and returns at approximately 4:00 PM. As you enter from Lane Avenue, park down on the left side along the fence near the gate between the two schools.
Tour cost per person is $1,295 Twin & $1,695 Single. No reservations accepted without a deposit of $350 per person. Make checks payable to Group Tours & Travel, and mail to the above address. Final payment is due September 1, 2021. Deposits are fully refundable if cancellation occurs on or before September 1, 2021. There are no refunds if cancellation occurs after September 1, 2021. Travel protection/cancellation coverage is available and recommended (approximately 10% of the total cost of the tour), but not included. One piece of luggage per person and one carry-on are permitted. Group Tours is not responsible for any delays, cancellations, injuries or circumstances beyond its control and reserves the right to change this itinerary. All trip components are subject to change in accordance with Government, State and Local guidelines and/or mandates. This tour will run rain or shine