Print Full Itinerary
Itinerary: Subject to change due to local conditions, unforeseen events, or more interesting as yet unplanned awesome experiences that become available
Overview:
What do you get when you combine the largest annual gathering of Tall Ships in North America with one of the most charming historic small towns in America and a little dash of bluegrass? The Sultana Downrigging Weekend!
So, let’s make our way south to the Eastern Shore of Maryland where we’ll find 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 festival day will be filled with music, sailing, ship tours, lectures, and exhibits among the tree-lined brick streets of captivating Chestertown. Further exploration will take us to the relaxed, sleepy bay towns of St. Michaels, Oxford, Easton, and Cambridge where each day begins with a peaceful, glorious view and ends at night in candlelight elegance.
Why not slip away on our southern adventure where we’ll toast to the Halloween season in quaint bayside towns, discover maritime and Chesapeake history, run from ghosts, and relax the night away!
Day One: Lums Pond State Park
As we make our way south, we’ll make a scenic leg stretching stop at the lovely Lums Pond State Park, Delaware’s largest freshwater pond.
Take a wander along the Swamp Forest Trail that winds around the picture perfect pond through serene wetland forests and browse the Whale Wallow Nature Center for interesting information on native flora and fauna.
Sinking Springs Herb Farm:
Now we make our way for a special treat 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 through creation of a thyme craft.
Olde Wye Mill:
As we continue south along Maryland’s Eastern Shore, we must stop at the Old Wye Mill that’s been grinding grain since 1682.
Take your time to wander through this technological time capsule and discover its age-old secrets.
Tidewater Inn:
Once we enter the idyllic small town of Easton, we’ll check into our charming rooms at the historic Tidewater Inn and relax before hitting the town filled with lovely restaurants for dinner and exploration on your own.
Day Two: African American Schoolhouse
Before our big Downrigging Festival day, let’s stop by the one room Worton Point Schoolhouse built for the African American community from 1890-1958 for a quick tour.
Sultana Downrigging:
Onto captivating Chestertown for some Downrigging Fun! Spend the day among the charming town filled with historic character from its uneven quaint brick streets to its beautifully maintained 18th century homes.
Step onto the decks of the fascinating Tall Ships and watch as they sail away (we’re hoping to be on one of them!).
Wetlands Preserve & Music Festival:
Take a stroll along the meandering trail of the Lawrence Wetlands Preserve that winds through meadows, woods, and wetlands.
If we don’t make the Tall Ship sail, enjoy the Music Festival Village where you can relax next to a cozy fire pit and dance to the rhythm of the best bluegrass bands in the region.
Find a tasty bite from local food vendors until the glow from the illuminated Tall Ships catches your eye. Once back at the comfy Tidewater Inn, have a great night’s sleep!
Day Three: Oxford Museum
Let’s step into the entrancing charm of the tranquil town of Oxford where the local museum will reveal 350 years of colonial history from when the town was one of the country’s earliest ports to the present day as a premier sailing destination.
We’ll follow the walking tour path through town to see the historic highlights and hear local stories straight out of the past.
Give your legs a rest while we relax for an included lunch at a fun local spot.
Splendid St. Michaels:
Now that your legs are ready to go, we’ll wander 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 stroll the randomly patterned brick sidewalks that take you past homes dating back to the mid-1600.
Cambridge Ghost Walk:
Once back at the Tidewater Inn, have a relaxing night here or join us as we travel to the charming Chesapeake town of Cambridge where we’ll grab a quick bite before a Ghost Walk on the most haunted street in Maryland.
Let’s leave the ghosts behind and head back to our warm, comfy Tidewater Inn for a peaceful night’s sleep.
Day Four: Mount Harmon
Before we say goodbye to the lovely Eastern Shore, we must visit Mount Harmon, a beautiful historic tidewater plantation set among a serene nature preserve.
With history spanning over four centuries, there will be a lot to learn on our guided tour of the 18th century manor house, colonial kitchen and hearth, smoke house and herb garden, replica slave quarters and tobacco barn.
Chesapeake City:
Let’s enjoy our last included local lunch in charming Chesapeake City set on the banks of the C&D canal.
North is now our direction as we make our way home to New Jersey filled with memories of Southern charm.
Pricing & Departures:
Departs Ridgewood Graydon Pool, corner of Linwood Ave & Northern Pkwy at 7:00 AM and returns at approx. 8:30 PM
Departs Madison’s Kings Road Parking Lot, 62 Kings Rd. at 7:45 AM and returns at approximately 7:45 PM
Departs South Plainfield High School at the end of Lane Ave at 8:30 AM and returns at approximately 7:00 PM
Price per person is $1,825 Twin & $2,275 Single. No reservations accepted without a deposit of $150 per person. Make checks payable to Group Tours & Travel and mail to the included address. Final payment is due August 5, 2025. Deposits are fully refundable if cancellation occurs on or before August 5, 2025. There are no refunds if cancellation occurs after August 5, 2025. Travel protection/cancellation coverage is available and highly 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.
Upon submitting final payment you are agreeing to our new policy.
Wet Blanket Policy:
Wet blanket
– a person who makes it difficult for other people to enjoy themselves by complaining, acting negatively, creating drama, etc.
– one that quenches or dampens enthusiasm or pleasure
- Our philosophy of travel involves getting out of the ordinary to experience other cultures and places with an open minded attitude and flexibility. Since as in daily life, anything can and will happen, let’s embrace these situations with acceptance and understanding because they will either lead to an unexpected, amazing experience or positive learning experience.
- If anyone brings along excess baggage such as incessant complaining, under the breath rude comments, outward negativity or other such behaviors that infect the entire group or individuals, we have the exclusive right to remove them from the tour at their own cost with no refunds. (yes, this means you)
- If any major concerns arise during a tour, please just come talk to us and we’ll work it out!
The Educated Wanderer
Group Tours & Travel
PO Box 35 Henryville, PA 18332
973-513-9001
