Every fall, the Northeast turns into a postcard with leaves of fiery reds, burnt oranges, and golden yellows. Or at least, that’s the dream. I planned a 9-day road trip through five states—New Jersey, New York, Connecticut, Rhode Island, and Massachusetts—timed to catch peak foliage. But Mother Nature was feeling her summer era, and I rolled through mostly green landscapes. Still, the trip delivered: small towns, prestigious universities, bookshops, historic homes, and coastal views. If you’re planning your own autumn adventure (and have slightly better timing), read on for the full itinerary.

Day One: DC to Princeton

From the DMV area, I drove north on I-95 for about four hours with a quick stop at one of the travel plazas.

The first destination was Grounds For Sculpture in Hamilton, NJ, a surreal, open-air museum that blends art and nature. We grabbed a bite at the Van Gogh Café on-site before exploring the winding paths and larger-than-life installations.

In the late afternoon, we drove to Princeton to wander around the ivy-draped campus and browse Labyrinth Books. After checking into our hotel for the night (Princeton Marriott at Forrestal), we wrapped the day with dinner at Aspendos, a cozy spot specializing in dishes inspired by the ancient flavors of Göbekli Tepe.

Day Two: Sleepy Hollow to Greenwich

After a quick breakfast in Princeton, I drove about two and a half hours north to Sleepy Hollow, NY. First stop: Kykuit, the Rockefeller estate, where we took the classic tour through the grand house, sculpture gardens, and underground art galleries. From there, we visited Sunnyside, the charming riverside home of Washington Irving, author of The Legend of Sleepy Hollow, for a guided tour steeped in literary history. Before heading out, we stopped for croquetas and made our way to Transom Bookshop, a cozy local gem. By evening, we arrived in Greenwich, CT, and checked into the Delamar Greenwich Harbor Hotel—right on the water and just steps from downtown.

Day Three: Hartford to Mystic

We left Greenwich behind and headed to Hartford—about two hours away—for what turned out to be one of the true highlights of the trip: the Mark Twain House & Museum. The tour through Twain’s home was not only beautifully preserved but brought to life by a guide who clearly loved the material and knew how to tell a story. If you’re even remotely interested in literature or American history, don’t miss this stop.

From there, we continued on to Mystic, CT, and checked into Harbor View Landing, a waterfront spot that felt like a peaceful exhale. We spent the afternoon strolling Olde Mistick Village, a quaint open-air shopping area with charming boutiques and a stop at Bank Square Books, a solid local bookstore with a great selection.

Now, here’s where I took a turn: in the evening, I drove about 25 minutes inland to Mohegan Sun Casino and fully indulged my inner degenerate. I ate dinner at Hash House A Go Go, an over-the-top favorite of mine from Las Vegas, and wandered the casino floor. For those less interested in slot machines and oversized chicken and waffles, Mystic offers more traditional dining options like Oyster Club or Red 36, both local favorites.

Day Four: Newport

From Mystic, I drove two hours east to Newport, Rhode Island, home to some of the most jaw-dropping mansions in the country. Built during America’s Gilded Age, these massive estates along Bellevue Avenue were once the summer “cottages” of families like the Vanderbilts. Several are open to the public, and you can easily spend a full day walking between them.

We visited The Breakers (pictured below), The Elms, and Rosecliff, but Marble House stole the show for me. Designed for Alva Vanderbilt, it’s as over-the-top as you’d expect, yet somehow still elegant. The mansion’s marble walls, ornate ceilings, and seaside setting made it feel like stepping into a European palace. Totally worth the walk, and honestly, I could’ve spent the whole day there.

By late afternoon, we drove an hour north to Providence and checked into the Christopher Dodge House, a cozy historic inn that’s walking distance from downtown. It was a quieter end to a day full of opulence.

Day Five: Providence to White Plains

We kicked off the day exploring a few gems in Providence, starting with the Rhode Island State House, which is open weekdays and worth stepping inside for the architecture alone. From there, we wandered over to the Providence Athenaeum, a beautifully preserved library that feels like something out of a novel, and then took a walk through Brown University’s campus. Highlights included the stately Carrie Tower and quick photo ops outside the John Hay and Sciences libraries. If you’re into browsing, Symposium Books nearby is a solid local stop.

After soaking up some Ivy League atmosphere, we drove about an hour and a half west into Connecticut for a brief but refreshing detour at Devil’s Hopyard State Park. Chapman Falls is an easy walk from the parking lot, and the sound of the water and quiet woods made it the perfect nature reset after a few city-heavy days.

We wrapped with a two-and-a-half-hour drive to White Plains, NY, and checked into The Opus Westchester, which is modern, sleek, and well-positioned for the next day’s stop in Hyde Park.

Day Six: Hyde Park

This was a day I’d been looking forward to: visiting Hyde Park, the home of my favorite president, Eleanor Roosevelt. (Yes, president. Don’t argue.)

Once in Hyde Park, everything we wanted to see was conveniently clustered within a mile, starting with the Eleanor Roosevelt National Historic Site. Val-Kill Cottage, where Eleanor lived and worked, was moving and inspiring, especially with the context provided by the Stone Cottage Visitor Center. Just down the road, we toured Springwood, the home of Franklin D. Roosevelt, and spent time at the FDR Presidential Library and Museum, which is impressively curated and full of personal details you don’t often find in larger museums.

In between, be sure to make a pit stop at Eveready Diner, a 1950s-style classic complete with chrome booths, thick malts, and slices of pie that should be illegal. Worth it.

If you have extra time (or a deep love of grand estates), the Vanderbilt Mansion nearby is also open to the public and is a nice way to end the day. Before heading to our hotel, we swung by Oblong Books in Rhinebeck, because no day is complete without at least one great indie bookstore.

We checked into Habitas-on-Hudson, tucked away in Staatsburg. It’s stylish, quiet, and surrounded by trees, a perfect place to unwind after walking in the footsteps of history.

Day Seven: Catskills to Worcester

We left Hyde Park in the morning and headed an hour northwest into the Catskills, a perfect blend of nature, kitsch, and small-town charm. First stop: the Catskills Visitor Center, where we stretched our legs by Esopus Creek and picked up a trail map or two. Just down the road, we couldn’t resist checking out the World’s Largest Kaleidoscope at the Emerson Resort. Yes, it’s touristy, but also trippy and oddly mesmerizing. Totally worth the five-minute detour.

Woodstock itself is as artsy and laid-back as you’d expect. We wandered along Tinker Street, stopping into cafés and shops, including The Golden Notebook, a great little indie bookstore. If it’s open, Opus 40—an outdoor stone sculpture park—is worth seeing, though hours can be spotty post–Labor Day. We also had the Martin Van Buren National Historic Site on the radar, but timing didn’t quite work out. (Pro tip: if weather or closures derail your plans, Art Omi, a contemporary sculpture park nearby, makes a great backup.)

By late afternoon, we had driven three hours to Worcester, MA, and checked into the AC Hotel downtown. It was a longer day, but it was full of contrasts: quiet mountain towns in the morning and city lights by night.

Day Eight: New Haven to Montclair

From Worcester, we made our way south to New Haven—about a two-hour drive—for a morning spent exploring Yale University’s stately campus. It’s everything you’d expect: gothic architecture, leafy quads (that were only starting to change), and the kind of academic energy you can feel in the air. We grabbed coffee and a bite at Atticus Bookstore Café, a cozy hybrid of baked goods and books that’s perfect for a midday pause.

From there, we took a scenic detour to Weir Farm National Historical Park, about an hour west. It’s a lesser-known gem in the National Park system, dedicated to American Impressionist painter J. Alden Weir. The grounds are peaceful, the studios are preserved with care, and the entire place feels like stepping into a living canvas. Definitely worth the stop, especially if you need a dose of quiet creativity after the buzz of New Haven.

By early evening, we landed in Montclair, NJ, and checked into The George. Of all the properties we stayed at, this one was my absolute favorite. A beautifully designed boutique hotel that honestly felt like a splurge and a sanctuary all at once. It’s owned and designed by Bobbi Brown and her husband, and each room has its own theme and name. We stayed in the Mike room, decorated with photographs of famous celebrities with the name Michael, from Michael Jordan to Jean Michel Basquiat. From the warm welcome to the plush details, to the secret snack closet, this place nailed it. After a week of packing and unpacking, I wished I had had an extra night to enjoy it longer, but alas, it was time to get home.

Day Nine: Headed Home

We kicked off our last day with a quick stroll through Montclair Book Center, a sprawling, delightfully unpolished indie bookstore packed with used and new titles across every genre. From there, we drove just ten minutes to Thomas Edison National Historical Park in West Orange, a must-visit if you’re even remotely curious about invention, innovation, or how many things one person can patent in a lifetime. The labs, the phonographs, the massive workspaces, you can walk through all of it.

Next up was Morristown National Historical Park, about 30 minutes away. This site played a crucial role in the Revolutionary War, and it’s one of the few places where you can walk through the same cold, hilly woods that Washington’s troops did during their harshest winter encampment. Watch the short film in the welcome center; it’s insanely humbling.

From there, it was back home—four hours to the DMV. In the end, we were about two weeks too early for peak foliage, but this road trip is great any time of year.

A Note of Thanks to Park Rangers

As I write this, we’re in the middle of a government shutdown, and many of the incredible national sites mentioned in this itinerary are temporarily closed. It’s a stark reminder of how essential, and often overlooked, our National Park Service and its rangers truly are. These stewards of history and nature are the ones who protect, preserve, and educate. Often doing so in uncertain conditions and without the recognition they deserve.

If you’re planning a visit to any of these sites, always check the official website beforehand to confirm hours, access, and availability. And when you do go, thank your ranger. Say it out loud. Buy something from the gift shop. Pick up your trash. Stay on the trails. Respect the land and the stories it holds.