Empire State Road Trip to The Finger Lakes and North Country, NY

A drive to the Finger Lakes and North Country in Upstate New York makes the perfect fall road trip if you are looking for some good, clean outdoor fun. It’s just over 4 hours from my town here in Connecticut. Often, I think of staying in New England in the autumn months and forget New York has so much to offer outside of the city. If you haven’t ventured to these regions in New York, add them to your travel list—you won’t be disappointed!

Our Accommodations

Recently, I had the pleasure of experiencing this scenic part of New York with my friends Helen and Mindy. We stayed at two hotels over our four-night stay that are part of the Harbor Hotel Collection. Our first stop on our Empire State Road Trip was a 2-night stay in Watkins Glen, New York. After weaving our way through picture perfect hills dotted with farms and spotting some early fall foliage along the way, we closed in on our destination.

Watkins Glen is as idyllic a coastal town as it gets. It is located on the biggest lake in the Finger Lakes, Seneca Lake. We arrived at the Watkins Glen Harbor Hotel and were immediately struck with glee because of its ideal location right on the water.

Leg two of our fall road trip took us to New York’s North Country with a 2-night stay in Clayton, New York at the 1000 Islands Harbor Hotel. This drive was just as breathtaking as the first and even more fall color started to emerge the farther north we traveled. The 1000 Islands Harbor Hotel is situated right along the St. Lawrence River which opens up to Canadian waters.

Upon check-in at each hotel, we took in the festive lobby that was decorated for autumn and set up with fresh apples, flowers, and cider for the hotel’s Apple Days celebration.

I shared a room with Mindy and it was very well-appointed and cozy. Comfortable beds, plush robes, and a huge bathroom with a Jacuzzi tub and two separate vanities plus a walk-in shower. Perfect for two friends to share. The rooms at Watkins Glen Harbor Hotel had a bright and cheery coastal country vibe and the rooms at 1000 Islands Harbor Hotel had a more lake living kind of feel with warmer colors and deeper tones in the decor.

Dining at both hotels was a real treat. With COVID safety on the mind, we chose to dine outside on the patio each morning and night and stayed warm with the outdoor fire pits and our Chappy Wrap blankets. (Dining inside is an option too.) The staff informed us the patio heaters were being turned on the following week to allow for more nights of outdoor dining. Meals were delicious and I really loved the Sea Scallops, Harvest Salad, and Miso Glazed Salmon. Other favorites were the French Onion Soup and Spiked Cider with Caramel Vodka.


I was happily surprised that each floor of both hotels set up a self-serve coffee and tea station for guests every morning 6:30am-10am with Starbucks coffee. I loved getting a cup and heading back to my room to get ready for the day or grabbing a cup to head outside to work on my laptop. The station was sanitized often and hand sanitizer was on the table for guests to use. The staff was very on top of making sure things were constantly cleaned and all the staff wore masks our entire stay. Guests also wore masks on the property. The only times I went without a mask was when I was seated at the dining table or in the privacy of our room.


I found the grounds of each hotel lovely with ample seating and Adirondack chairs with views of the water. I loved working here in the mornings curled up in a chair enjoying my surroundings. Why work from home, when you can work taking in a lovely view every morning?!

Our days were filled with outdoor fun and each town had plenty to enjoy. Here’s how we spent our time in each location…

Things We Enjoyed in Watkins Glen, NY

  • Hiking at Watkins Glen State Park This park just underwent a 6.5 million dollar renovation. The waterfall views are just spectacular here and in a few weeks the fall foliage will really be something to behold. There are several trails and overlooks to stop at and enjoy along the way.

  • Boat Tour of Seneca Lake Aboard Captain Bill’s Seneca Lake has a rich history and this hour-long tour will give you views you can only get from the water. There is plenty of room to spread out and masks are required.

  • Wine Tasting at Lakewood Vineyards This is a great stop on the Finger Lakes Wine Trail and has an award-winning selection of locally produced wines. This family-operated vineyard will steal your heart with its lake views and resident pups.

  • Go Apple Picking at Reisinger’s Apple Country With a great selection of apple varieties to choose from, Reisinger’s is a lovely family-owned orchard complete with homemade cider donuts and a pumpkin patch. I recommend the Jonagolds and Galas!

The downtown of Watkins Glen is worth the short walk from the hotel too. Plenty of restaurants, shopping, and great murals painted on brick buildings all throughout the downtown. Watkins Glens International Nascar Racing is depicted all around town in the murals and checkered sidewalks.


Things We Enjoyed in Clayton, NY

  • Take a Tour of Boldt Castle A short drive from the hotel, we crossed over 1000 Islands Bridge and took the 3-minute ferry over to Heart Island to see this amazing property. You’ll think you’ve been transported to Europe and you’ll marvel at the architecture and history.

  • Visit the Antique Boat Museum Right in Clayton is this gem of a museum with every wooden canoe, sail boat, and motor boat to behold. There are over 300 unique and wonderfully preserved boats to admire along with a great history lesson. They even have craftsman restoring the boats on site for you to see.

  • Ride the River on Miss 1000 Islands III While at the Antique Boat Museum, be sure to book some time on the water with Captain Ed and cruise in style aboard this wooden power boat beauty! This tour of the St. Lawrence river will take you past lighthouses, gorgeous lake homes, the 1000 Islands encampment, and you can even wave at Canada!

    During our stay, the downtown was under construction and new sidewalks and landscaping were being installed with beautiful paver details. It will be so lovely to walk those sidewalks when they are finished soon. Shops and restaurants line each side of the downtown.



We loved our fall road trip up to the Finger Lakes and North Country in New York! It was a much needed mini-break and kicked off the fall season for us all! Be sure to check out the Harbor Hotels Collection. These are all 4 Diamond Award-winning hotels and they offer great amenities. We loved our stay and felt safe and comfortable during this pandemic. Road trips are always my preferred mode of travel and being able to get out and explore a ‘new to me’ place was a joy.

I’ll be sharing more activities from our trip in detail this week. After picking apples, hiking, and spying some early fall foliage, I am ready for all things autumn!

Pin for Later


Be sure to visit Style Inherited next and read her recap of our Watkins Glen visit.

A special thank you to Watkins Glen Harbor Hotel and 1000 Islands Harbor Hotel for hosting our stay and road trip. All opinions are my own.

Until next time,


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