Fall is one of the most magical times of the year when we see all the greenery of summer turn into colors of bright yellow, orange and red as we slowly head into sweater weather. If you’re a fall-fanatic like myself, then it’s likely you’re obsessed with all things fall too. I think its imperative that everyone take a fun road trip at least once in their lives. But even more encouragingly during the fall season. There’s just nothing like it.
I’ve lived New York, West Virginia and Northern California and nothing compares to the fall season in New England and upstate New York. I knew that ever since moving to Massachusetts, I had to take a formal road trip during peak fall foliage to experience the best of the best when it comes to fall. With some of the most beautiful foliage in the area, we had an amazing time driving through the countryside, seeing some of the most amazing landscapes, farm houses, animals and mountains.
While there are many routes to take, we drove through Western Massachusetts, pass The Berkshires and Albany, making our way to upstate New York near The Finger Lakes. The first leg of the trip took 5 1/2 hours while the second leg took 2 1/2. Our return drive was close to 8 hours but it didn’t feel like it. The roads are quiet, there’s no major cities causing traffic. And the views are just to die for. Totally worth it and hassle-free.
We followed our route as planned out by The Harbor Hotel Collection.
They offer a full itinerary on the website, guiding you and suggesting the best places to make stops and the most enjoyable things to do in the area. The entire itinerary focuses on traveling through upstate New York starting with 1000 Islands, then Chautauqua and finally Watkins Glen. Since we we drove from the east we made our first stop at Watkins Glen and then made it to Chautauqua. We didn’t make it to 1000 islands based on our schedules. But had an amazing experience visiting the places we did. I highly recommend this road trip if you’ve never been through upstate New York as it’s the most quiet and quaint place to be during the fall.
Fall Foliage Road Trip
The best part about this road trip was leaf peeping, seeing all the fall colors and turning mountain corners with wide, stunning landscapes and views. While we didn’t make a ton of stops, there are plenty of places to stop and explore on your way to Watkins Glen from Massachusetts. Between Boston and Watkins Glen you can find Gillette Stadium, Concord, Worcester, The Berkshires, Providence, Springfield, Hartford (one of my personal favorite places), Lenox, Albany, Saratoga Springs, Ostego and Ithaca.
Depending on how much time you have, making select stops can really maximize your experience by slowing down and exploring places you may have otherwise missed if you drove right by it. As for the timing of your road trip, I highly suggest planning it for mid October to early November to get the prime fall foliage possible. But do keep in mind that this is a wonderfully beautiful trip even late into the fall. The scenic drives are beautiful in every season.
Where to Stay
Watkins Glen Harbor Hotel
As the first hotel on our fall foliage road trip, Watkins Glen Harbor Hotel surely did not disappoint. It’s a beautiful expansive property residing right on Seneca Lake with views of the water and sunrise right from your window. I was throughly impressed with the fall decor both indoors and outdoors as well. When you pull up to the front doors, there’s hay barrels, pumpkins and other favorite fall decor that invite you inside to their cozy lobby equipped with a fireplace, more fall decor and a hot coffee station.
While the hotels seems to be a bit understaffed right now from the aftermath of the pandemic, they were attentive and as helpful as possible with all my questions that I always have when visiting hotels. I’m fascinated by properties and the history, which is prevalent at the Harbor Hotels in upstate New York.
We stayed at Watkins Glen Hotel for 2 days and were able to experience the amenities, dining options, fitness and business center as well as the surrounding area.
Upon arrival to our guest-room we were welcomed with a cheese plate and white wine to get the trip started. It was a very comfortable place to stay as the temperatures indoors were perfect. The beds were spacious and plush, the robes were lush and the staff was kind and accommodating.
As an AAA Four Diamond Hotel, they offer a plethora of amenities during your stay including complimentary high-speed WI-FI service throughout the hotel, a hairdryer, iron, ironing board, fridge and a high definition flat-screen TV in the guestroom, breakfast, lunch, dinner and cocktails at the Blue Pointe Grille and Coldwater Bar, access to The Patio for al fresco dining overlooking Seneca Lake, an outdoor fire-pit, indoor swimming pool and hot tub, a fitness and business center, The Harbor Ballroom and adjacent function areas comprising 6,000 sq. ft. of space to accommodate up to 300 guests, 24-hour room service and a wonderful complimentary coffee and tea bar on each guest floor.
As for food, we ate breakfast and dinner at The Blue Pointe Grille offering classic American cuisine.
We enjoyed foods like salads, fresh soups of the day, salmon, pasta, steak, dessert, delicious cocktails and draft beers. The overall ambiance and atmosphere were very enjoyable and relaxing and I loved that you could have dinner at Coldwater Bar for a more laid-back bar-like atmosphere or in the dining room of Blue Pointe Grill, yet still had access to the same menu.
Overall, the location of being right on Seneca Lake and having access to the downtown area so close by made our trip more enjoyable and convenient.
Chautauqua Harbor Hotel
The second hotel on our trip was Chautauqua Harbor Hotel. Two and a half hours even further north took us to this stunning property residing on Chautauqua Lake. While Watkins Glen was thoroughly enjoyable, this property was my personal favorite. There’s a beautiful and historic lighthouse that you drive up to upon arrival, a gorgeous and detailed lobby, large outdoor space facing the lake with games and fire pits as well as an outdoor bar. Being that the hotel is a bit newer, it felt fresh and inviting everywhere you went.
The room was setup very similarly to Watkins Glen except the decor and architecture was more updated and modern. And we had our very own balcony facing the waterfront views. There was a bottle of red wine and chocolate waiting for us upon arrival and a reflection of fall trees on the lake that I’ll never forget. Truly the most ideal place to relax in luxury!
I’m also a huge fan of luxury robes so checking the robe situation is something I do almost immediately when staying at hotels. I absolutely loved the robe from here because it was thinner, light-weight, has a hood, short sleeves and a beautiful grey color as opposed to traditional white.
We stayed at Chautauqua Harbor Hotel for 2 days and were pleasantly pleased with our experience from a comfort, privacy, nightlife and hospitality perspective.
The amenities you have to look forward to when you stay here include 135 deluxe guest rooms and suites, breakfast, lunch, and dinner available at Lakehouse Tap and Grille, Carousel Bar overlooking Chautauqua Lake, indoor and outdoor pools, outdoor fire pits, the Pier Ballroom and Conference Center with 450 person capacity and over 10,000 square feet of meeting space, an outside banquet patio, on- site professional Concierge, a fitness and business center, bellman service, coffee and tea stations on every floor and luxurious bedding.
Our dinner experience at Chautauqua Harbor Hotel was great because the bar area was large, lively and inviting. Although the menu was almost identical to Watkins Glen hotel, we some new seasonal options and fun cocktails to try. We enjoyed the lobster dip, smoked wings, raviolis, Indian curry soup, steak, the lobster rolls, the mai tai cocktails as well as their impressive smoked penicillin margarita
Overall, we loved our stay at Chautauqua Harbor Hotel especially because it was raining most of our trip and we still got to have fun and be cozy inside.
What To Do For A Fall Foliage Road Trip
Watkins Glen
Glen Mountain Market Bakery & Deli
As a New Yorker myself now residing in New England, I wanted to get my hands on a classic New York sandwich when visiting. We headed to a popular place called Glen Mountain Market Bakery & Deli where they serve breakfast sandwiches, lunch sandwiches and specialty coffee drinks. It was the perfect place to fuel up before our outdoor adventure and kept us full for hours.
Watkins Glen State Park
As one of the most popular and well-noted things to do in the area, a stop at Watkins Glen State Park is a must. If you want to experience some of the best fall foliage, colors, hiking trails and waterfalls, this is the place to do it and you definitely won’t be disappointed.
Watkins Glen State Park was definitely one of the highlights of our road trip through upstate NY. As the fall foliage and waterfalls were in their prime. The park has several hiking trails and is considered moderate on most paths. If you walk straight through, it takes about an hour. And if you make stops here and there to really enjoy your time, it’ll take about 2-3 hours. The park is free to enter and has 7 trails and 19 waterfalls waiting inside for you. The pathways are easy to follow and there’s always something interesting at every corner.
While I’m not much of an extreme hiker, I am a sucker for a good view. Some of the best view points include Sentry Bridge, Glen of Pools, Rainbow Falls, Cavern Cascade and the Gorge Trail.
Seneca Wine Trail
Did you know the Seneca Lake Wine Trail is the largest and most active wine trail in New York? Right in the heart of The Finger Lakes Wine Country you’ll find The Seneca Wine Trail attracting visitors and travelers to experience its rich history, beauty and production of world-class wines. With 35 wineries on The Seneca Wine Trail, you’ll come across a variety of wines including Riesling, Chardonnay, Cabernet Franc and Pinot Noir.
After our adventure at Watkins Glen State Park, we made our way to Lakewood Vineyards where we were greeted by stunning views, friendly staff, adorable dogs and delicious wine. Lakewood Vineyards is known to produce some of the regions most savory and award-winning wines. The property is large with wine & mead, picnic areas, shops and the ability to take a stroll around the winery. Tastings are $5 per person and if you decide to buy a bottle, you get $3 of your tasting back. Such a good deal!
The winery is a 6 minute drive from Watkins Glen State Park. And a 5 minute ride back to Watkins Glen Harbor Hotel. A convenient and ideal way to spend an afternoon in upstate NY.
Chautauqua
Tim Horton's
Tim Horton’s is a popular coffee and donut fast-food chain that is best known in Canada. Up until our visit to Chautauqua, I had never visited one and boy was I pleasantly surprised. As a Dunkin’ lover myself, I was excited to try an alternative coffee and donut place. And it surely did not disappoint. It was warm, clean and inviting inside with a plethora of fresh donuts to choose from and fun coffee selections. I went with the classic frosted donut and sprinkles with crispy donut flakes and crunchy sprinkles, a delicious warm hash-brown and their creamy pumpkin iced coffee.
If you’ve never been to a Tim Horton’s before, I highly recommend checking it out for a special treat.
National Comedy Center
As someone who isn’t a huge fan of museums, I do have to say that this is one of the best I’ve been, to if not the best. The National Comedy Center is a museum located in Chautauqua, dedicated to comedy.
Tickets are $25 a person and allow you to have access to the entire museum and create a profile upon arrival. The profile is created on a screen in the lobby that allows you to put your name. And select the type of humor you have based on your favorite comedy movies, shows, actors and comedians. You get these digital wristbands that allow you to check in and out of the digital exhibits. Making it super personal, innovative and interactive. We spent so much more time in this museum than we expected, laughing and having an awesome time. I highly recommend this as a must-do when you visit Chautauqua.
Lucille Ball Desi Arnaz Museum
If you didn’t already know, Lucille Ball, the star from I Love Lucy, is from Chautauqua NY. Her house is here, she’s buried here and there’s an entire museum dedicated in her honor. You can do a dual admission for both The National Comedy Museum and Lucille Ball Desi Arnaz Museum for $30. Otherwise you can visit this museum for only $16. In the museum you’re able to explore the lives, careers and legacy of Lucille Ball and Desi Arnaz while immersing yourself in an experience of original costumes, awards and exact creations of the I Love Lucy sets.
Labyrinth Press Company
Labyrinth Press Company is an eclectic restaurant and bar with fantastic vegetarian and vegan fare, coffee, beers on tap, artwork and good vibes. We came here after our visit to The National Comedy Center for some food and beers. And it was a really unique experience. I loved the quaint downtown street, the bar atmosphere, the drinks and the kind locals mingling about.
What To Wear For A Fall Foliage Road Trip
For a fall foliage road trip, I prefer trendy, comfortable, neutral and practical. I make sure to bring plenty of leggings, cropped sweaters, pants, jeans, beanies, boots, sneakers, coats and umbrellas. When the weather gets colder, the suitcases get thicker, so thakfully a road trip allows you to pack as much as you want since you typically have a car the whole time!
Cropped Sweater, Leggings and a beanie
This is one of my all time favorite looks for fall. There’s nothing like a good pair of leggings, a comfortable, cropped sweater paired with boots or sneakers and a cute beanie to throw on top and add some attitude. I typically shop at Amazon, Fabletics and Lululemon for these types of articles of clothing. Leggings are a staple for any trip and are always a comfortable option. What I love most about cropped sweaters is they are typically loose-fitting. So you can wear a tank top underneath and take the sweater off if you need to. I always prefer dressing in layers for trips because I hate being hot. The beanie adds style but also keeps you warm when you get out of the car to explore a bit. It also looks super cute in photos!
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Sweaters, Jeans and Boots
Another classic look and one of my favorites for jumping out of the car and doing more activities like going to a restaurant or a winery. A comfortable, interesting patterned sweater paired with a good pair of jeans and boots will never steer you wrong. The fall is my favorite time to wear all kinds of sweaters, because they are appropriate for most outings. I typically shop at Amazon, Express, Levi’s and Abercrombie & Fitch for these articles of clothing.
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Athleisure Looks for Activities
Planning to pack and wear 1-2 athleisure outfits is always a good idea as leaf peeping typically involves outdoor activities and hiking. I like dressing in layers by wearing leggings, tank tops, long sleeves, jackets, sneakers, rain boots or hiking boots depending on the weather and terrain. I typically shop at Lululemon, Fabletics, Amazon, Columbia, Sperry, North Face and Adidas for these articles of clothing.
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Sweaters and Pants or Skirts
You can’t forget about some fancier outfits! And by fancy I mean sweaters paired with pants and skirts instead of leggings and jeans. I told you the sweater love was real! I typically shop at Amazon, Express, Nordstrom and Abercrombie & Fitch for these articles of clothing.
THE GOODS
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