If you’re looking for the perfect fall road trip, look no further than Watkins Glen, New York! I can’t believe this was my first time experiencing the Finger Lakes region. I certainly hope it won’t be my last, though! Between the stunning vistas, the charming towns, and seemingly endless vineyards, there’s something for everyone to enjoy in upstate New York! Keep reading for my entire trip itinerary, insider tips, and more details on my Empire State road trip this fall!

*Please note that we wore masks our entire trip,
unless we were able to safely social distance while outdoors.

Our Road Trip Up To
The Finger Lakes

From Fairfield County, Watkins Glen, NY is only a four and a half hour drive! As someone who grew up driving down to North Carolina each summer to visit my grandparents (a thirteen-hour drive), this road trip was easy breezy. Plus, I had the best company! I traveled with my two friends and fellow bloggers, Kristy of @kristynewengland and Mindy of @mindybriar.

Getting to spend an extended amount of time with Kristy and Mindy was so nice! As a blogger, most days are spent just working by myself, which can get lonely! These 4 days away really filled my cup getting to collaborate with these amazing ladies!

When you’re driving up to the Finger Lakes, you HAVE to stop off at the Oak & Reed restaurant in Middletown, NY. Oak & Reed is only a quick ten minute detour off route 17. It’s the best restaurant in the area with an ever-changing menu featuring thoughtful and innovative cuisine. Either eat-in or take your food with you on the road.

For the rest of your road trip up to the Finger Lakes you’ll be surrounded by gorgeous fall foliage. The countryside vistas almost seem too good to be true!

Where We Stayed

We stayed at the Watkins Glen Harbor Hotel, which is part of the family-owned Hart Hotels award winning “Harbor Hotels Collection.” Why work from home, when you could work from here?! In full disclosure, our stay was comped in exchange for sharing our experience. As always, all opinions are my own! Hopefully this goes without saying, but I’ll never agree to go on any press trips that I wouldn’t be willing to pay for myself.

And before I get into sharing all the amazing details from our stay with the Watkins Glen Harbor Hotel, I wanted to say a HUGE thank you to everyone who made our experience special, especially Lisa, thank you!

The Watkins Glen Harbor Hotel is located right on Seneca Lake. Fun fact, Seneca Lake is the largest of the Finger Lakes and has a maximum depth of approximately 600 feet! We had the opportunity to cruise around the lake on the Seneca Legacy, which is docked right across from the hotel. During our boat ride around Seneca Lake we learned all about this region’s history, the booming salt industry, and more!

(While Seneca Lake is fresh water, the salt refineries sit atop rich underground salt reserves.)

Pro Tip: Make sure you book a lake-view room with a jacuzzi tub for the ultimate experience. These oversized jacuzzi tubs were the perfect way to wind down after an adventure-filled day! Additionally, if you’re not comfortable with eating out right now, you can book a suite with a kitchen to do your own cooking/to enjoy take-out.

We took full advantage of the hotel’s amazing outdoor spaces during our stay. We enjoyed each of our meals at the Blue Pointe Grille outdoors and while the temperatures did get a bit chilly, we just brought a blanket with us and bundled up!

Everything on the breakfast menu was delicious! For dinner, I especially loved the scallops and salmon! I so appreciated how willing the staff were to accommodating my dietary restrictions!

What To Do In
Watkins Glen This Fall

Sit Out On The Seneca Lake Pier //

The Seneca Lake Pier is perhaps the most photographed spot on Seneca Lake. I loved enjoying my morning tea on the pier wrapped in my ChappyWrap. It was so nice and tranquil out on the lake that early and I loved just taking in the scenery! One morning I even swore I saw an otter scurry across the dock!

Go Hiking In Watkins Glen State Park //

Watkins Glen State Park recently underwent 6.5 million dollars in renovations including new look-outs and educational materials. With 19 waterfalls and miles of trails to explore, this is the perfect place to spend a morning or afternoon!

Shop My Entire Hiking Outfit Below:

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Pro Tip: Make sure you wear a good pair of boots, preferably hiking boots. It will most likely be muddy/wet along the trails, which is why sneakers aren’t a great idea. These are my hiking boots that I LOVE. I wore them the entire time I was in Iceland so I can confidently say they are the real deal! If you’re looking for a shearling-lined option, check these out!

Tour & Tasting at Lakewood Vineyards //

Vineyards abound the Finger Lakes region and I would definitely recommend making time for a few of them. On our trip we visited and toured Lakewood Vineyards, which is just a quick 5 minute drive up the road from our hotel.

This family-owned and operated vineyard produces award-winning wines and you get to taste them in the most picture-perfect setting. The vineyard sits on a hillside that crests down to Seneca Lake, which makes for absolutely stunning scenery to enjoy their delicious wines.

I purchased a couple of bottles to bring home with me and I am happy to report back that they taste just as good at home as they did at the vineyard! If you visit any other vineyards on your trip, let me know what you think of them! I’d love to include a few more in this post!

Pick Your Own Apples at Reisinger’s Apple Country //

Reisinger’s Apple Country is about a 10 minutes drive from the Watkins Glen Harbor Hotel. It’s a must visit for more gorgeous countryside views and for delicious & fresh picked apples! Their orchards offer a variety of apples for eating and for baking. I made an apple pie with my apples and it was delicious!

Before you leave, make sure you stock up on their freshly made apple cider donuts!

What To Pack For
Your Fall Road Trip

Check out my full blog post on what I packed for my perfect fall road trip here!

One of the many reasons why I love a good road trip is that you can wayyyy over pack! As my grandma always says, “you’ve got room in the car, so why not bring it?!” On this road trip up to the Finger Lakes I was so glad to have packed plenty of extra pieces to stay cozy & warm the whole time!

Here are a few of my must-have items
for the perfect fall road trip:

ChappyWrap Blanket // It’s really more than a blanket, it’s a lifestyle. Do I sound crazy for saying that? Maybe, but I also know that anyone who already owns a ChappyWrap blanket and is reading this is nodding their head in agreement! This blanket kept me warm while enjoying breakfast and dinner outside each day, spending a lovely afternoon at Lakewood Vineyard, boating around upstate NY, and more!

Dudley Stephens Fleece // These turtleneck fleeces are made sustainable in the USA by a local to Greenwich, CT company. How cool is that?! Not only will these keep you nice and warm, they are effortless to style! For sizing, I’d suggest staying true to your size unless you are busty/have broad shoulders, in that case you’ll probably want to size up 1 size.

LL.Bean Boots // There are few things more classic New England than a pair of Bean Boots, am I right?! If you opt for a shearling-lined pair, you’ll be able to keep your feet nice and warm while also keeping them dry!

Barbour Jackets // I’ve got an entire blog post dedicated to my love for Barbour Jackets here! They’re so well made, last for years, and never go out of style! These are the two styles I own and love: the Barbour Beadnell Waxed Cotton Jacket and the Barbour Cavalry Diamond Quilted Jacket. I wear a size 2 in both of them. If you want to layer underneath your quilted Barbour, then I’d suggest going up 1 size.

Stay tuned for my blog post recapping our time up in Clayton, NY at the 1000 Islands Harbor Hotel
and our trip to the Boldt Castle!

Have you planned your
perfect fall road trip yet?

I’d love to know where you plan on heading this fall! Comment below with your upcoming travel plans. And of course, if you have any questions about my trip, please don’t hesitate to reach out via DM on Instagram (@styleinherited) or via email (helen@lifeonphillipslane.com).

Before you go, check out some other fall road trip ideas to New England towns with the best fall foliage!