The Ultimate New York Road Trip

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If taking an upstate New York road trip during the fall isn’t on your bucket list yet, it's about time you added it.

Now, I know it’s only the beginning of summer. You probably aren’t thinking about fall yet (unless you live in Arizona and you’re already tired of triple digits like me).

But with the nationwide rental car shortage, it is imperative to plan ahead to secure a reasonably priced rental car. Fall will be here before you know it!

Granted, New York is fun no matter what season. I visited Central Park several years back during spring’s cherry blossom blooms. While it was an unforgettable experience, too, there really is no place like the northeast in autumn.

The air is crisp but comfortable. Apple trees are ripe for the picking. Fall foliage is rich and various on every hillside. Pumpkin-everything tastes better where you can wear a sweater (my fellow Phoenicians know what I mean). And, with students back in school, many attractions receive less crowds during weekdays.

After attending a friend’s wedding last fall, I took an upstate New York road trip through gorgeous, colorful countryside in search of both hidden gems and must-see destinations. While I knew that not all of New York was like New York City, I was still pleasantly shocked how rural and laidback the rest of the state is.

Since my friends got married near East Stroudsburg, PA, due to COVID restrictions in New York, that is where we started our journey. But this New York road trip itinerary can work regardless where you begin.

5-day Upstate New York Road Trip Itinerary

Remember all those connect-the-dots games you played in kindergarten? Well, planning a road trip on Google Maps is much the same for me. Just like I planned our Utah honeymoon road trip, I love the challenge of finding an effective route that also hits all the highlights.

Once I set my start and end destinations, it is a lot easier to fill in the route in between. And for this New York state road trip, the middle of our route was a golden nugget called the Finger Lakes region.

This small area is loaded with history, museums, natural beauty, areas for outdoor activities, farmers markets, spas, and more.

Day 1

Fuel your morning early at a coffee shop like the King’s Gambit for some quality espresso. Then, if you follow your nose, it will lead you to sugar-crusted apple spice donuts and fresh-squeezed cider at Mackey’s Orchards.

Your first stop is Bannerman Castle, about 1 hour and 20 minutes north of NYC. Located on an island in the Hudson River, this mostly intact castle is open for tours and full of history. To get there, you can board a ferry from one of two locations or self-guide a rental canoe over to the island. Then, take a 1.5 hour walking tour of $30.

From there, head north toward the Catskill Mountain Railroad. Depending on your interests, this might be a yay or nay. While we enjoyed the slow-moving locomotive ride, it wasn’t as scenic or lush with fall foliage as I had hoped. However, it was only $16, so definitely not a waste! If you’re taking small children, the train would definitely keep them fascinated.

Once you’re back in the car, your next stop at the Kaaterskill Falls Viewing Platform is only another 40 minutes up the highway. If you have time to hike the stairs down, you really should. But the falls are just as stunning from any angle!

If you have any interest in seeing the town of Woodstock, where the largest concert in American history took place, it’s technically on your way back down toward Interstate 86/Highway 17.

Ideally though, if you had an early start on this first day, you’ll want to end your drive near or outside of Liberty, NY, just in time for dinner at The Kaatskeller. Serving wood-fired pizzas and gelato, their garden is open for outdoor dining and warmly twinkles with bistro lights. They also offer takeout.

Day 2

The best part about this 5-day road trip itinerary is it works for non-morning people. We didn’t get an early start any of the days and we were still able to see everything we wanted.

This morning stretch is about a 2.5 hour drive to Ithaca. But, thankfully, it’s a beautiful one, and fairly open when we visited. Surprisingly, most of the drive is rural farmland.

Although Ithaca is a well-known tourist hub, it still has a small, college town vibe that makes you feel at ease. There’s a pile of things to do here. From a local science center, the Ithaca Farmers Market, edgy eateries with urban graffiti walls, the Cornell Botanic Garden, and waterfall hikes, Ithaca could be an all-day affair.

If hiking and waterfalls are your thing, check out Buttermilk Falls State Park and Ithaca Falls Natural Area. The latter is completely free, right in the heart of Ithaca’s downtown and more of a pretty walk along the river than a hike.

Grab a bite from the Ithaca Bakery to enjoy by the falls, or head over there for dine-in and prime people-watching. All ingredients come from local sources and their baked goods are made in-house daily.

Warning: their menu is lengthy. All the yummy sandwich and soup options had my indecisive brain spinning. But I finally opted for Laura’s Sweet Surprise on a gluten free bagel. Pulled pork, melted manchego, and caramelized onions combine with a strawberry balsamic jam and, oh man, now I want this sandwich delivered, pronto!

If you need more caffeine to go (of course you do), try their Ithaca Falls special. Chocolate and strawberry meet a dirty chai blended in foamy oat milk to create one of the most unique drinks I’ve ever tasted. I was clearly on a strawberry kick when we dined here and I regretted nothing.

After lunch, head to Robert H. Treman State Park or Taughannock Falls State Park – or both! Personally, I’d say if you’re short on time and want to choose only one, go with Taughannock.

At 215 ft., this waterfall is the tallest falls east of the Rockies. Watch it from a high viewing platform as it powers down into the natural gorge, or take a walk through the falling leaves to get right up to it on ground level.

Depending on your timeline, you may choose to stay in the area this evening.

But if you have time to travel a little further north, Chimney Bluffs State Park is a little over an hour north of Taughannock Falls.

This park sits on the southern shores of Lake Ontario, halfway between Syracuse and Rochester. Explore the unique rock formations, woodland trails, or rent some equipment for water activities if it happens to be sunny the following day!

Day 3

First of all, Shequaga Falls Park really isn’t a park. Simply drive through Montour Falls, NY, park at the end of the main road into town, and walk up to the falls overlook area. If there’s been adequate rainfall, this waterfall really can be impressive and worth a stop if you just need to stretch your legs.

Plus, it’s only 8 minutes away from Watkins Glen State Park.

This park was by far one of our favorite stops. For one, hardly anyone was there. Surrounded by fall foliage, naturally carved black stone walls, bridges, and tunnels set a moody tone for the various falls and pools throughout the area. Each angle was a photographer’s paradise.

You will want to spend quite a bit of time at this location to see all attractions along the trail. While it is not a difficult hike by any means, you will get a lot of steps in. You’ll also want to watch your step as the stone paths are consistently wet and slippery.

If you finish at Watkins Glen in late afternoon, you may want to stay in the area or at least drive 1.5 hours west to get a closer start on the next day’s activities.

Day 4

We arrived mid-morning to Letchworth State Park, just before the crowds started to gather. Known as the Grand Canyon of the East, Letchworth features three beautiful falls powered by the Gennessee river. The Middle Falls drops about 107 ft. and is illuminated by lights from May to October.

Here, the tree colors were more vibrant than in southern and central New York. Although the air was cool close to the water’s spray, the sun glowed warm that day and we were quickly shedding our layers after climbing so many steps.

As it’s a popular spot, there is a Lower Falls Restaurant and four snack bars within park vicinity. You can bring in your own food to grill at any of the available campsites. Just remember to carry all your waste out!

If your legs are up for another hike, head an hour northwest to the Eternal Flame Falls. What makes these so special? In short, there is an organic gas produced by decomposing shale, and, when the wind hits it just right, a small flame is lit behind the waterfall.

Keep in mind, if the weather has been consistently warm and dry, these falls will be, too. However, if you’re up for it, admission is free and the trail is about an hour in-and-out.

After all that hiking and driving, a hearty lunch at Zoup! Eatery in Orchard Park, NY, is just what your belly needs. Their menu offers soup, salad, sandwiches, and healthy grain bowls. Try their grilled cheese sandwich strips and a bowl of Santa Fe Chicken Chili; it’s the definition of comfort food.

Make your way into Niagara for the evening. I suggest staying as close to the falls as possible for convenience. Although it is a tourist city, the residential area of Niagara isn’t well-maintained.

Day 5

Time for a whole day of exploring Niagara Falls!

But first, coffee at SPOTcafé. If your hotel doesn’t offer free breakfast, or you simply miss it, fear not. Breakfast is served all day at SPOT.

Now, you all know me. I’m the independent, DIY advocate. But trust me when I say that hopping on a tour is totally better than trying to navigate all the highlights yourself.

Yes, it’s free to walk into the park and check out the falls from above.

But with a combo ticket, a Maid of the Mist ferry gets you right up close to both American and Horseshoe Falls. Then you get to don another plastic poncho to experience Cave of the Winds where the force of the falls pummels above your head.

I don’t care if it’s “touristy,” it’s a must-see attraction for a reason!

Our local tour guide had historical insight, great dad jokes, and the hook-up on an authentic Italian bakery.

See, if nothing else, you’ll be helping the local economy survive as it tries to pick up after a year of lockdowns.

At the time we visited, and at the time of writing this blog, the Canadian border was closed to Americans. Supposedly, there are a lot more attractions and things to do on the other side. While I would love to drive on into Toronto one of these days, I don’t feel like we missed out on anything in Niagara.

At sunset, choose to take a stroll along the boardwalk to listen to the roar of the falls. Then hang around until the multicolored lights appear on the water’s surface.

There are plenty of chain restaurants for dinner, including the Rainforest Café and Hard Rock Café. But if you want something unique, try Savor at the Niagara Falls Culinary Institute, which features an open kitchen and seasonal menu.

New York Road Trip - Maps List & Total Drive Time

Farm Stands - Honorable Mentions

There are plenty of orchards and family farms out along the old highways. Many of them are not even advertised on Maps.

As I mentioned, we went to Mackey’s in New Jersey just before the wedding. We took a hayride up to the orchard to pick our own fresh apples then splurged on fresh cider and donuts on our way out.

But if you’re traveling through central and upstate New York, here’s a list of other farms and markets to check out:

Tantillo’s Farm in Gardiner, NY

The Apple Farm in Victor, NY

Pick’n Patch & Corn Maze in Stanley, NY

The Great Pumpkin Farm in Clarence, NY

What to Pack

Shoulder seasons are difficult to prepare for, but that’s also what makes them the best times to travel. Prices and crowds are lower and the weather is usually tolerable.

Still, it’s wise to pack layers.

Think tights or leggings and comfortable but stylish boots. If you limit your packing to one carry-on like I do, bring shoes that can both be worn on a nature trail as well as a dine-in restaurant later on.

Pack light sweaters and flannels you can remove if the sun is out.

Bring a packable, light rain jacket, like this Columbia one that’s currently 50% off.

Where to Fly

Just a thought, you can always start or end your journey in the Big Apple. You will definitely want a couple of days at least, though, so plan accordingly.

If you’re flexible where you begin and conclude your New York road trip, I suggest comparing prices between airports and rental cars.

Sometimes you might find a great deal to fly into a smaller airport, but then the rental car is outrageous. Oftentimes, too, one-way rental car itineraries like mine curate increased tax. But sometimes dropping off your car at an off-site location and taking a Lyft to the airport can save you chunk of cash as well.

Just keep swapping dates, airports, and drop-off locations to lock in the best deals.

For the record, Southwest operates in LaGuardia, Long Island, Albany, Rochester, and Niagara/Buffalo. Google Flights, Kayak, or Priceline are also helpful in finding the cheapest deals and booking both flight and car in one session.

Since we visited just before another big lockdown in the state of New York, it’s hard to say what the highways and sites look like in “normal” times. But travel restrictions and mask mandates have eased, so expect tourism in New York to be on the rise again this fall.

Final Tips: Upstate New York Road Trip

I always like to over plan. But it’s not because I structure each day rigidly. I just like to have options.

I prefer to have a route mapped with a list of things to do at every stop so I’m not scrambling for what’s next or taking a risk on something I didn’t research.

As always, no matter how well you plan, there will be some attractions you forego for another time. Sometimes it’s due to weather or traffic, or simply what you’re feeling at the time.

While I would have loved to travel into Vermont to hop aboard the Green Mountain Railroad and get lost among maple leaves, it just wouldn’t fit into the timeline.

We also crossed our fingers tight that the Canadian border would be open at Niagara by the time we arrived, but we had no such luck (considering it’s still closed a whole year into this pandemic).

If you are wanting to enjoy the changing of leaves as much as possible, plan your dates accordingly. We visited the first week of October, which was still a bit early for some parts but perfect in others.

Remember, out east, everything is so much closer. You can cover more ground and road trip attractions in less time because the states are small in comparison to the west coast.

No matter if you pack your itinerary full or keep it wide open, a New York road trip is the perfect way to celebrate fall this year. I hope you can make it!