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Experience the enchanting beauty of the Hudson Valley in the fall, where the crisp autumn breeze carries the scent of crunchy leaves underfoot. The Hudson Valley transforms into a breathtaking tapestry of reds, oranges, and golds each fall offering a stunning backdrop. Begin your journey in the legendary Sleepy Hollow, exploring historic sites like the Sleepy Hollow Lighthouse and cemetery. Wander the opulent grounds of the Rockefeller Estate Visitors Center and the Gothic grandeur of Lyndhurst. Cruise the serene Hudson River, taking in vibrant foliage along its banks. Delve into history at the FDR Museum & Library and the grand Vanderbilt Mansion. Walkway Over the Hudson offers breathtaking panoramic views, while Val-Kill Cottage and West Point Military Academy enrich your tour with historical significance and natural splendor. This tour definitely offers a great array of variety, dont miss out!
Click here to view a full brochure complete with day-by-day itinerary
Tour Includes:
Tour Pricing:
$3750 per person Double
$4,570 Single
Non-Members Add $30
Activity Level 3: Moderate
Expectations: Expect a moderate amount of walking. There will be time to rest on the coach and between attractions. To enjoy this tour, you should be prepared to walk slightly longer distances, climb stairs and tolerate periods of standing, for example on city walks, sightseeing stops or ship excursions. The daily pace and timing can fluctuate significantly between longer and shorter travel days, with additional activities possibly occurring in the early morning or evening. There may be some changes in altitude or temperatures. Please be aware that on tours with flights and cruises you will be required to handle your own luggage and walk longer distances in airports and cruise terminals. In addition, you may need to handle your own luggage at hotels where luggage handling is not available.
Appropriate for: Most travelers beginning with those who are moderately fit, lead semi-active lives, are comfortable participating in long days of activities and expect some physical exertion.
Travel Protection:
We recommend that you purchase a
travel protection plan to help protect you and your travel
investment against the unexpected. Unforeseen events such as
flight delays, baggage loss or even a sudden illness or injury
could impact your travel plans. For your convenience, we offer
a Travel Protection Plan provided by the United States Fire
Insurance company and administered by Trip Mate, Inc.; in UT
and CA, DBA Trip Mate Insurance. To review full plan details
online, go to www.tripmate.com/wpTPD040 for domestic tours valued up to $4,000 per person or to www.tripmate.com/wpTPG040 for all international tours or domestic tours valued over
$4,000 per person.
Day 1
Day 1: Monday, October 6
Embark on a picturesque autumn adventure through the vibrant Hudson Valley aboard a comfortable Burlington Trailways motorcoach! Depart from the available location of your choice, where your friendly host and skilled driver will ensure a seamless and enjoyable journey. As the rich hues of fall surround you, sit back and relax, knowing rest and refresh breaks are thoughtfully planned along the way along with a lunch break before continuing toward your first destination. After an included dinner at the Maumee Bay Brewing Company, arrive in Oregon, Ohio, to a warm welcome and a restful overnight stay, setting the perfect tone for the memorable journey ahead.
Day 2
Day 2: Tuesday, October 7
After enjoying an included breakfast at the hotel, the journey continues with a scenic drive to Das Dutch Haus Restaurant and Bakery. Here, you’ll fill up on a delicious group lunch, followed by some time to explore their charming bakery. It’s the perfect opportunity to pick up freshly baked treats or unique goodies to enjoy later on the tour. Following a rest and refresh break as needed, the day concludes with an overnight stay at the SpringHill Suites Scranton Montage Mountain in Moosic, PA. Dinner this evening is on your own, with a variety of inviting restaurants within walking distance of the hotel to suit every taste.
Day 3
Day 3: Wednesday, October 8
Start the day with breakfast at the hotel before checking out and heading toward the enchanting town of Sleepy Hollow, NY. The journey begins with a visit to the Rockefeller Estate Visitor Center, where you’ll embark on a guided tour of Kykuit, the stunning hilltop home of the Rockefeller family. This grand estate offers breathtaking views of the Hudson River and showcases beautiful architecture, gardens, and an impressive collection of art, including works by Picasso and Warhol.
Next, you’ll enjoy lunch and some free time to explore the charming downtown area, brimming with unique
shops and historic character. The afternoon features a walking tour of the iconic Sleepy Hollow Cemetery, where you’ll delve into the life and legacy of Washington Irving, famed author of The Legend of Sleepy Hollow. Learn about his enduring literary contributions while visiting his final resting place and other notable sites in this storied cemetery.
Cap off the day with a warm welcome dinner at Pete’s Saloon and Restaurant before settling into your hotel for a relaxing two-night stay, perfectly situated to explore more of the Hudson Valley.
Day 4
Day 4: Thursday, October 9
Begin the day with a leisurely breakfast at the hotel before heading to Washington Irving’s Sunnyside, a charming riverside estate steeped in literary history. Nestled along the Hudson River, this picturesque Gothic Revival home reflects Irving’s imagination, filled with period furnishings, artifacts, and stories that bring his life and works to vivid detail. Stroll the beautifully landscaped grounds and enjoy the tranquil atmosphere that inspired one of America’s first great writers.
Next, take a lunch break on your own in downtown Tarrytown, NY, where quaint eateries and inviting shops provide a delightful stop. The afternoon continues with a visit to the Lyndhurst Welcome Center, offering insights into this grand Gothic Revival mansion. Built in 1838, Lyndhurst is surrounded by stunning grounds and is renowned for its elegant architecture, interiors, and scenic views of the Hudson River.
A stop at the iconic Sleepy Hollow Lighthouse provides a perfect photo opportunity with its striking silhouette against the water, capturing the spirit of this historic region. Then, enjoy an included group dinner at a local restaurant before experiencing the evening’s highlight—the Great Jack O’Lantern Blaze! This spectacular event features thousands of intricately carved, illuminated pumpkins arranged in dazzling displays, from towering sculptures to themed scenes. Set on the historic grounds of Van Cortlandt Manor, the Blaze showcases a blend of art and history with its roots in traditional fall celebrations.
After this magical experience, return to the hotel to rest and prepare for the adventures that await the next day.
Day 5
Day 5: Friday, October 10
Begin the day with a hearty breakfast at the hotel before checking out and setting sail on a scenic Hudson River Cruise aboard the Rip Van Winkle II. Glide along the majestic river, taking in stunning views of historic lighthouses, grand mansions, and the vibrant fall colors that paint the landscape in shades of gold, red, and orange. As you relax and enjoy the crisp autumn air, you will have an included boxed lunch to eat while marveling at the beauty of Hudson Valley’s iconic scenery.
After the cruise, continue to the Locust Grove Estate, a National Historic Landmark and former home of artist and inventor Samuel Morse. Morse was an accomplished artist and inventor, best known for developing the Morse code and revolutionizing communication with the invention of the telegraph. Beyond his technological achievements, he was also a celebrated painter, creating works that reflected his talent and creativity. This elegant Italianate villa, set amidst 200 acres of lush gardens and trails, offers a glimpse into 19th-century luxury. On the guided tour, explore the beautifully preserved interiors filled with period furnishings and artwork, as well as learn about Morse’s fascinating life and contributions to technology and art.
In the late afternoon, arrive at the Hampton Inn & Suites in Poughkeepsie, NY, where you’ll have time to refresh before heading out for a memorable dinner at Shadows on the Hudson. Perched on a bluff overlooking the Hudson River, this upscale restaurant is renowned for its breathtaking views, contemporary ambiance, and delectable cuisine. With its panoramic windows and warm atmosphere, Shadows on the Hudson provides the perfect setting to end a day immersed in the beauty and history of the Hudson Valley.
Day 6
Day 6; Saturday, October 11
The day begins with an included breakfast at the hotel before heading to the Vanderbilt Mansion in Hyde Park, NY. This stunning Gilded Age estate, once home to Frederick and Louise Vanderbilt, showcases the opulence of one of America’s wealthiest families. Set amidst beautifully manicured gardens and overlooking the Hudson River, the mansion is a testament to the grandeur of the era. Hyde Park itself is rich in history and charm, known as the home of several notable estates.
Next, visit Staatsburgh State Historic Site, the elegant country home of Ogden Mills and his wife, Ruth Livingston Mills. This Beaux-Arts mansion provides a glimpse into the lavish lifestyles of New York’s elite during the late 19th and early 20th centuries, offering insights into the social dynamics of the time.
Lunch is included at Foster’s Coach House, a historic restaurant offering warm hospitality and hearty fare. Known for its colonial charm and rich history, Foster’s has been a beloved dining spot in Rhinebeck for generations.
In the afternoon, explore Val-Kill, the only National Historic Site dedicated to a First Lady. As Eleanor Roosevelt’s retreat, Val-Kill reflects her simple yet impactful way of life. On the guided tour, you’ll visit three rooms on the first floor, learning about her work advocating for human rights and the legacy she shared with Franklin D. Roosevelt.
The day continues with a visit to the Walkway Over the Hudson, a historic railroad bridge transformed into the world’s longest elevated pedestrian walkway. On a guided group tour, learn about the bridge’s fascinating history, from its industrial past to its modern role as a stunning vantage point for panoramic views of the Hudson River and surrounding landscapes.
Dinner this evening is included at the Palace Diner, a classic eatery offering a relaxed and nostalgic dining experience. After a satisfying meal, return to the hotel for a restful evening, reflecting on the rich history and scenic beauty of the day’s adventures.
Day 7
Day 7: Sunday, October 12
Start your Sunday with a leisurely breakfast at the hotel before checking out and visiting the Franklin D. Roosevelt National Historic Site. This historic location was the lifelong home of FDR, the 32nd President of the United States, who led the nation through the Great Depression and World War II. On the guided tour of Springwood, his beloved estate, you’ll explore the rooms where Roosevelt crafted policies and find personal touches that offer a glimpse into his family life and presidency. The site also includes stunning grounds that reflect his passion for conservation.
Next, enjoy an included group brunch at Restaurant 1915, located within the historic Bear Mountain Inn. Built in 1915, this iconic inn combines rustic elegance with natural beauty, nestled in the heart of Bear Mountain State Park. The restaurant offers scenic views and a delicious meal in a warm and inviting atmosphere, perfect for a relaxing break.
The journey continues to the U.S. Military Academy at West Point for an engaging combined motorcoach and walking tour. Discover the history and traditions of the “Long Gray Line,” a term that refers to the generations of cadets who have trained at West Point. Learn about the rigorous life of cadets, their academic and military training, and the academy’s crucial role in preparing future leaders. Highlights of the tour include a stop at the Cadet Chapel, a stunning Gothic Revival structure with the world’s largest church pipe organ; the Plain, a historic parade field surrounded by striking architecture; and Trophy Point, a scenic overlook featuring monuments and breathtaking views of the Hudson River.
Dinner is a farm-to-table experience at the Summit Alter House, where fresh, locally sourced ingredients create a memorable meal. After dinner, travel back to the SpringHill Suites Scranton Montage Mountain for an overnight stay, preparing for the journey home after a day steeped in history and inspiration.
Day 8
Day 8: Monday, October 13, 2025
Begin the day with breakfast at the hotel before departing for a day of travel. Rest and refresh breaks will be taken as needed, along with a stop for lunch along the way. The highlight of the afternoon is a visit to the Pro Football Hall of Fame in Canton, OH. This renowned museum celebrates the history of professional football, honoring the greatest players, coaches, and contributors to the game. Explore fascinating exhibits, including interactive displays, historic memorabilia, and the Hall of Fame Gallery, where bronze busts of football legends are proudly displayed.
Dinner this evening is included at The Twisted Olive, an upscale yet casual dining destination set amidst the beautiful landscapes of Canton. Known for its creative menu featuring modern twists on classic dishes, the restaurant offers a memorable dining experience in a stylish and inviting atmosphere. Afterward, check in at the Hampton Inn & Suites for a relaxing overnight stay, wrapping up a day of travel and exploration.
Day 9
Day 9: Tuesday, October 14
The day begins with breakfast at the hotel before traveling to Millersburg, OH, for a visit to the Amish and Mennonite Heritage Center. Here, you’ll learn about the rich history and traditions of the Amish and Mennonite communities during a 30-minute guided tour of Behalt, an extraordinary 10-foot-tall, 265-foot-long cyclorama. This colorful mural artfully depicts the history, culture, and religious beliefs of these groups, from their European roots to their life in America today.
Next, meet a step-on guide for a “Backroads Amish Tour,” where you’ll explore the picturesque countryside and visit local Amish homes and businesses, gaining an authentic glimpse into their way of life. The tour includes a traditional “Haystack Meal” lunch, a unique Amish dish in an Amish home. This dish features layers of ingredients like meat, cheese, vegetables, and sauces served buffet-style. Very similar to the making of a taco salad. This hearty and communal meal is often enjoyed at gatherings and offers a delicious taste of Amish hospitality.
After saying goodbye to your guide, travel to Toledo, OH, for dinner at the famous Tony Packo’s Café. Known for its Hungarian-inspired menu and iconic hot dogs, Tony Packo’s gained fame thanks to frequent mentions on the TV show MASH* and its tradition of autographed hot dog buns lining the walls, signed by countless celebrities. Enjoy the flavorful dishes and lively atmosphere of this Toledo institution.
End the day with an overnight stay in Oregon, OH, preparing for the journey home tomorrow after a memorable experience immersed in history, culture, and delicious food.
Day 10
Day 10: Wednesday, October 15
On the last day of travel, we make a memorable stop at the Studebaker National Museum in South Bend, IN, where you can step back in time and explore the history of the iconic Studebaker brand. This fascinating museum showcases classic automobiles, wagons, and a rich collection of artifacts from the company’s storied past, giving you a glimpse into the evolution of transportation and the legacy of this American manufacturer.
Afterward, enjoy a lunch break on your own before continuing the journey back home. As we reflect on the wonderful experiences of the past few days, we remember the delightful time spent exploring the Hudson Valley, from the historic homes and scenic landscapes to the legends of Sleepy Hollow that brought the region’s fascinating history to life. The new friends made along the way and the shared stories and laughter are what make each trip truly special. We can’t wait for you to travel with us again soon—there are more adventures to come!