Chasing the Headless Horseman in Sleepy Hollow
We spent two weeks road-tripping through New England. Along the way, we visited Sleepy Hollow for all things Headless Horseman, Jamestown, New York (the hometown of my favorite redheaded comedian), Niagara Falls on both the U.S. and Canadian sides, enjoyed leaf peeping in Vermont and New Hampshire, explored Portland Harbor in Maine, and toured the mansions of Rhode Island.
We began our trip with a few days in Sleepy Hollow, our favorite place to visit for Halloween. The weather was lovely, and we enjoyed walking around Sleepy Hollow and Tarrytown, taking in the charming towns and festive Halloween decorations.
One of our favorite activities is Blaze, which features thousands of carved pumpkins on display. It is absolutely incredible—the designs and large-scale displays are truly impressive. We enjoyed walking through it so much that once we reached the end, we turned around and did it all over again.
The next day, we tried several new activities that hadn’t existed during our last visit in 2019. At Philipsburg Manor, we experienced The Headless Horseman Files (a whodunit mystery centered on the disappearance of Ichabod Crane), Spirits of Sleepy Hollow (a magic and illusion show inspired by the Headless Horseman), and Twilight Village (a combination of shows and activities throughout the manor grounds).
The Headless Horseman Files was a guided tour through the manor buildings. In each one, you meet a character from the story who shares gossip about the local residents, their own theories about what happened to Ichabod Crane, and some wonderfully juicy details. It was very well done, and the performers were fantastic.
Spirits of Sleepy Hollow was a fantastic magic and illusion show, with tricks themed around the Headless Horseman legend. There was some audience participation, and a few of the illusions genuinely left us in awe.
We ended the day at Twilight Village, which took place across the manor grounds. There was storytelling, dancing, fire throwing, and even an appearance by the Headless Horseman. Food and merchandise stalls were scattered throughout, making it a fun and atmospheric evening.
Back to Jamestown: A Lucy Pilgrimage
We made the long journey across the state to Jamestown, New York—the hometown of Lucille Ball and home to a museum dedicated to her and I Love Lucy. I was lucky enough to visit once before, back in 2011, with my mom, grandma, and great-grandma. We had a fantastic trip, and I’ve always wanted to return. Since then, I’ve successfully brainwashed Ben into becoming a fan of the show, so I was especially excited to bring him along this time.
We spent a full day at the Lucy Desi Museum. There is so much to see, from fascinating behind-the-scenes information to memorabilia from the show, along with fully recreated sets—including the Ricardos’ apartment and the Hollywood Hotel. We had an amazing time, and Ben left with an even greater appreciation for the show.
After the museum, we drove around town visiting other Lucy-related sites, including her childhood home, her resting place, and a park featuring a statue in her honor.
The next day, we visited the National Comedy Center. I wish we’d had more time there—our main focus had been the Lucy museum, so our visit felt a bit rushed. There are countless displays, audio clips, and videos, and it really deserves several hours to fully experience. We especially enjoyed watching clips from famous comedians—so funny.
Mist, Chocolate, and Thunderous Views
Our next stop was Niagara Falls. We stayed overnight in Buffalo—yes, we had buffalo wings for dinner—and visited the falls that evening before spending the following day exploring. Visiting at night was especially fun, as we were able to see the falls lit up. The view would probably have been even better from the Canadian side, but since it was a quick evening visit, the U.S. side worked well.
The next day, we started on the U.S. side. Ben did the Maid of the Mist boat ride, while I opted to stay dry. I hate being wet and didn’t want to risk spending the rest of the day soggy, so I stayed up on the cliffs, enjoyed the views, and took photos of Ben’s boat. He absolutely loved the experience and came off the boat buzzing with excitement—and surprisingly, he didn’t get that wet!
After the boat ride, we crossed into Canada via the Rainbow Bridge. It was an easy walk, with a quick stop at passport control, and then we were in Canada. While crossing the bridge, Ben spotted what he swore was a giant Hershey’s Kiss in the distance (yes, really). His chocolate radar was correct, and we soon found ourselves at the Hershey store. Of course, we couldn’t resist picking up a few treats for later.
After our chocolate detour, we continued along the cliff edge, enjoying the views until we reached Journey Behind the Falls. This experience takes you through tunnels with openings directly behind the waterfalls, and one exit brings you incredibly close to the crashing water. While we were there, police were conducting training exercises and were abseiling down the side of the falls, which was surprisingly fun to watch.
Being that close to the waterfalls is incredible—the sound, the mist, and the sheer power of the water really put things into perspective.
We then continued on to the Niagara Power Station. No longer in operation, it’s now a museum dedicated to the history of hydroelectric power. During our visit, there was a Nikola Tesla exhibit (the man, not the car company), including a Tesla lightning bolt display with hourly demonstrations.
Inside the museum, you can access the old tunnels beneath the power station. It’s a bit of a walk, but at the end you emerge at water level, right near the falls. The views from there are absolutely stunning.
Afterward, we slowly made our way back to the Rainbow Bridge and crossed back into the U.S. There is a small entry fee when returning (around $1 or so), payable by cash or card, followed by U.S. passport control at the end of the bridge.
Breaking Up the Drive in Rochester
When planning our road trips, I always try to find interesting stops along the way to break up longer stretches of driving. In Rochester, I came across the George Eastman Museum. George Eastman was the founder of Kodak, and the museum is located in his former home.
I was hoping to learn more about Kodak as a company and the history of film photography, but that aspect felt a bit lacking. There was information about George Eastman’s early life, how he became interested in photography, and a brief overview of the founding of Kodak, along with a display of old cameras. However, the main focus of the museum was several art galleries featuring photography. While they were interesting to see, I had been hoping for more in-depth history on photography itself.
One highlight was getting to explore Eastman’s former home. It’s a beautiful mansion—I especially loved the dining room and the conservatory—and I was impressed by the built-in organ that still plays music throughout the house.
While I wouldn’t go out of my way to visit the museum, it made for a pleasant and worthwhile stop to break up a long drive, and we still enjoyed our time there.
Maple, Leaves, and Covered Bridges
We spent a few hours in the gorgeous town of Woodstock, Vermont. This is the town that comes to mind when you think of classic Vermont! Visiting in October was especially beautiful, with colorful leaves falling all around as we enjoyed some leaf peeping. The town is full of charming shops, restaurants, delicious ice cream spots, and even a picturesque covered bridge.
Nearby, we stopped at a maple tree farm. They had a small museum explaining how maple trees are tapped, how sap is collected, and how it’s transformed into maple syrup. In the shop, we got to sample their syrup—so good—and browse a huge selection of maple-based food products.
We also walked a short loop trail through the woods to see some of the trees actually being tapped. It was fascinating—I had no idea how maple syrup was made!
Lighthouses and Coastal Charm in Portland
Since our sailing lessons earlier in the year, we’ve become really interested in all things water-related, including lighthouses. Naturally, we had to stop in Portland to see them. We got lucky—Spring Point Ledge Lighthouse was open for tours, and it happened to be the last day of the season! You can walk up to the lighthouse for free, but a guided tour inside requires a ticket. Tickets can be purchased with cash at the lighthouse, or by card at the shop along the shore before walking out on the rocky pier.
The tour was fantastic. We got to explore all parts of the lighthouse, including the kitchen, bedrooms, and the light rooms. The life of a lighthouse keeper is so fascinating. When lighthouse keepers lived there, there was no pier—supplies and access were only by boat. The pier was added later.
After the tour, we drove around the area to view other lighthouses. These aren’t open to the public, so you can only see them from the outside.
The next day, we headed into the town of Portland. We had considered taking a bus tour, but it was late in the day, and we had missed all of the tours. Instead, we enjoyed walking around the town, grabbing a late lunch, and doing some shopping.
Newport’s “Cottages” of the Gilded Era
I was so looking forward to our visit to Newport to see the “cottages.” Several mansions are open to the public, but since we were visiting late in the season, only four were available for tours: The Breakers, Marble House, Rosecliff, and The Elms.
The Gilded Age was such a fascinating time, and after visiting the mansions, I read a few books about the women of Newport, including Alva Vanderbilt and Marjorie Post.
Marble House
Built between 1888 and 1892 as a summer “cottage” for Alva and William Kissam Vanderbilt (the grandson of the Commodore), Marble House became a social landmark. It helped transform Newport from a relaxed summer colony of wooden houses into the city of opulent stone palaces we know today. The mansion cost $11 million at the time—equivalent to about $285 million today.
The Breakers
After Marble House was completed, Cornelius Vanderbilt II, William’s brother, built his summer retreat nearby between 1893 and 1895. The original mansion on the grounds burned down in 1892, so The Breakers was designed to be as fireproof as possible, using masonry and steel trusses with no wooden parts. Cornelius even required that the boiler be placed underground beneath the front lawn, far from the house.
Rosecliff
Built from 1898 to 1902 by Theresa Fair Oelrichs, a silver heiress from Nevada, Rosecliff was modeled after the Grand Trianon of Versailles. Its ballroom was featured in the 1974 film The Great Gatsby, the iconic ceiling appears in the opening credits of The Gilded Age TV show, and the mansion’s façade was even recreated on a New York City street for season 1.
The Elms
Constructed between 1899 and 1901 for coal baron Edward Julius Berwind, The Elms drew inspiration from the 18th-century Château d’Asnières in France. Berwind was fascinated by technology, and The Elms became one of the first American homes wired entirely for electricity, with no backup system. It also featured one of the first electrical ice makers, making it one of the most technologically advanced homes of its time.
Roadtrip Ends, Orlando Begins
After an incredible two weeks exploring New England—from the spooky streets of Sleepy Hollow to the mansions of Newport—it was time to say goodbye. The colorful leaves, charming towns, and historic sites had made for a memorable journey, but now we were ready to trade autumn scenery for sunny skies and a week of fun in Orlando with Nicole’s family.