As the summer sun begins to wane and the air takes on a crisp, invigorating chill, there’s no better time to embark on a breathtaking journey through the picturesque landscapes of western Connecticut and Massachusetts, particularly the enchanting Berkshires region – and from New York, you can be on your way to fall foliage bliss within a couple of hours.
Nestled on the outer borders of New England, this area comes alive with a vibrant tapestry of reds, oranges, and yellows during the fall season, making it a prime destination for a memorable autumn road trip. While maybe not as well-known as the well-trodden Vermont and New Hampshire fall foliage routes, these areas excel in offering their own version of classic New England autumn charm.
With this itinerary, you’ll embark on a mesmerizing adventure through stunning leaf-peeping spots, charming towns and hidden gems, ensuring that your road trip offers a classic celebration of the season’s splendor. So pack your bags, hop in a rental, and get ready to witness the magic of fall in western Connecticut and the Berkshires!
Why this itinerary
For first-timers, I would personally recommend the Vermont and New Hampshire itinerary I designed for our fall foliage trip last year. I do believe it’ll give you the more classic New England fall season ~vibes~!
However, I understand that for those not flying into Boston, it can be a bit of a hike to get to VT/NH. Despite being “LAX to Luxury,” the city with the highest concentration of my audience is actually New York, and I thought it would be fun to come up with a fall foliage itinerary that would be easy to execute for NYC dwellers!
Like the VT/NH itinerary, this one takes you through historic small towns, multiple apple cider donut stops and lots of changing leaves, only totaling about 9.5 hours of driving total over four days.
When to go
Fall foliage peaks at different times in different areas in different years which can make planning and trying to nail the peak a bit of a crapshoot! Because Mount Greylock is at a higher elevation, the colors will change sooner there than Litchfield County, CT. For that reason, you’ll probably find that it’s hard to nail peak colors in both regions.The early- to mid-October range will likely be your best bet for seeing the range of colors from early to full peak.
If you’re looking at other fall foliage hot spots or want information specific to this year, search for current fall foliage forecasts. Old Farmer’s Almanac, NewEngland.com and SmokyMountains.com offer their own broader forecasts with the latter two offering interactive maps. Because it’s not an exact science, the forecasts from different sources may differ, so I like consulting each of these.
Pick up your rental car at any NYC location – there are plenty around the city. Do note that unlike airport locations, non-airport rental locations may only have a grace period of one hour from the start of your rental to pick it up until you’re marked as a no-show, so be sure to try to estimate an accurate pick-up time!
After you pick up your rental car, start your drive about two hours north to Litchfield County, CT. Your first stop will be Averill Farm, which has a gorgeous farmstand of gourds, mums, and – most importantly – apple cider donuts and cold apple cider! You can also wander the orchards for a leisurely stroll while consuming your apple goodies. They also offer apple picking if you want to commit to a whole bag of the fruit.
Grab sandwiches from The Po Cafe right on the Washington, CT green, which came highly recommended by a local.
Next, make your way to Lake Waramaug. While the trees here change a bit later than areas further north in this itinerary, the hills around this lake do come alive with some exceptional fall foliage views if you time it right. Just up from the shores of the lake, stop by Hopkins Vineyard for a sip of local wine and a cute store with local goods. To be completely honest, the wine wasn’t my favorite, but we enjoyed the chance to get out of the car and walk around this lakeside hill.
Where to Stay
We spent the first night of our trip at the Mayflower Inn & Spa, an Auberge property, hosted by the property. This was a bucketlist hotel for us and it lived up to the hype for the perfect luxury country escape!
While The Mayflower is definitely an all-season resort and would be a treat anytime, fall is an amazing time to visit as New England autumn colors come alive here on their 58 acres of gardens and woodlands. This itinerary calls for a one-night stay as it is a road trip, but I’d highly recommend coming back in the future (at any time of year) and spending at least a few days here to explore it in full.
The Mayflower is probably best known for its massive spa which is truly incredible (a day trip to the spa is also a popular city escape option!), but they’ve actually become quite a culinary destination as well. They recently brought on a new Michelin-Starred Executive Chef, José Ramírez-Ruiz, and the menus across the two restaurants have been revamped to have a hyperfocus on local ingredients, including some foraged finds from right on the property. The Garden Room menu in particular was such a unique vegetable-forward delight.
We stayed in the Signature King with Fireplace which was notably spacious and had modern, bright New England vibes in its styling. As a group of three, I really appreciated that the property was able to accommodate a rollaway bed, which this room category had plenty of space to accommodate.
Base rates can be as low as $600 in the winter but hover around $1300-$1900 and up in busier seasons.
After a delicious breakfast at the Mayflower, check out and start driving north, first stopping in the cute town of Kent, Connecticut. I was surprised by how charming I found Kent; I had included it in the itinerary for the state park and covered bridges, but didn’t expect to be so taken by how delightful the town itself was!
Nothing says classic New England fall foliage road trip itinerary like a covered bridge, and luckily, there are a few in this area – driving north from the Mayflower, you’ll first pass by Bulls Bridge, and further north you’ll also find the West Cornwall Covered Bridge.
After Bulls Bridge, stop by Kent Greenhouse & Garden for a stroll on your way into the town’s main strip. Grab a hot bevvie (we loved the rocking chairs outside of Wilson’s) and don’t miss House of Books a few doors down – it’s a must-visit.
A little further north, you’ll find Kent Falls State Park which wins points for having easy parking, a pedestrian covered bridge, and very easily accessible waterfalls flanked by gorgeous trees that frame the rushing water with bright fall yellows.
Where to Stay
To be familiar with my content is to know that I endeavor to see the positive in a lot of my travel experiences. I mitigate a lot of potential expectation misalignment issues with extensive research and seek excruciating amounts of detail prior to any given stay, flight or experience. In short, I typically don’t have very negative things to say because my expectations are appropriately set based on my prior research.
That being said, I had high expectations for the luxury property I booked for our time in Lenox. Unfortunately, I felt the experience in person fell vastly short of those expectations in every regard, from the hard product to the service. I share this not to be a Negative Nancy, but to prevent you from making the same mistake – thus, I do not recommend the Wheatleigh.
Since I can’t recommend where we actually stayed, I’d recommend checking out Miraval Berkshires for a luxury alternative. We didn’t originally book Miraval because I view it more as a spa/retreat destination and we designated our time at the Mayflower to scratch that itch for the trip, but I’ve heard great things from friends who have stayed there. You can also redeem Hyatt points for a stay!
For a non-luxury option, Life House Berkshires offers a great balance of value with a younger, newer atmosphere than most other Lenox-area options. We stayed at Life House for our third night after leaving the Wheatleigh. Our rate at Life House was around $600/night which itself isn’t a great value for what it is (it’s basically a design-forward converted motel), but almost every other night that same week averaged around $200/night, which I think is a great rate for what you get.
The third day of this itinerary is dedicated to nature!
Crank your engine for a car-hike up Mount Greylock – there are tons of walking hikes here as well, but I loved having the option of taking the scenic byway up to the highest peak in Massachusetts until that road closes at the end of October! Have your navigation direct you to the Visitor’s Center and follow Rockwell Road up. With higher elevations you typically get fall colors sooner, and those colors were popping when we went. If visibility is expected to be low, you’ll still be able to enjoy the colors on the road, even if the various view points aren’t as fruitful.
On your way back to Lenox, stop by Bartlett’s Orchards for an apple cider donut – these were my favorite of the trip! They also had amazing produce grown on their own land. If we were staying in a vacation rental and cooking our meals, I would’ve loaded up here!
After getting your daily dose of apple-tinged sugar, head to the Pleasant Valley Wildlife Sanctuary. There’s a small welcome center where you’ll pay $5 in admission for adults, and from there you’re free to explore miles and miles of beautiful trails alive with the richness of the changing leaves. I loved that they also had a wheelchair-accessible all-persons trail.
Wrap the day up with dinner at Prarie Whale in Great Barrington. This was my favorite meal of the trip (my friend Allie, who was on the trip, is so great at finding spots like this!). From the cauliflower special to the insane cornbread, everything we had was a hit.
Where to Stay
Ideally, you’re staying at the same place for both nights in Lenox! We switched from Wheatleigh to Life House as noted in the “Where to Stay” description for night two.
As I mentioned in day two of my VT/NH itinerary, finding a local fall festival is a great way to mingle with local communities while celebrating fall. We went to the Harvest Festival at the Berkshires Botanical Garden to start our last day of this road trip! It wasn’t as well-rounded with crafts, antiques and food options as I would’ve hoped (there were a lot of random vendors like septic tank companies), but we loved strolling the grounds of the gardens.
Once you’ve had your fill of fall-festival fun, grab tickets for a self-guided visit of The Mount, which was Edith Wharton’s estate. The estate has been beautifully restored with lots of great information about Wharton, and the gardens are lovely to stroll.
For one last small-town hurrah, stroll Stockbridge’s bustling main street, and then on your way out of town, stop by Taft Farms for one last apple cider donut. From here, it’s only a three-hour drive back to NYC!
For NYC-dwellers who don’t want to make the hike all the way north to Vermont and New Hampshire, there are closer options that still give you a taste of New England fall! From the fiery hues of the foliage to the charming towns, delicious dining and serene countrysides, this road trip has something for nature enthusiasts, history buffs, and those who appreciate the simple pleasures of strolling small New England towns alike. Whether you’ve wandered through the historic streets of Stockbridge, hiked to breathtaking vistas, or savored an apple-spiced treat at a local cafe, the variety of experiences on this trip will help scratch the itch for autumn hues until fall rolls around again!