A Leaf-Peeper’s Paradise: Four Days of Fall Foliage Fun in Vermont and New Hampshire

You never know what you have ‘til it’s gone, right? That’s how I feel about fall foliage – growing up in a beautiful corner of upstate New York, I always took the changing colors and general celebration of fall for granted. Now that I live in Los Angeles, I have to make an effort and travel to experience the vibrant hues of autumn in all their glory!

Every year I swear I’ll make my New England leaf-peeping dreams come true as the crisp winds of September usher in these spectacular color changes, and last year, I finally did. After tons of research, I planned a quintessential fall foliage itinerary across New Hampshire and Vermont, where lush forests turn into a mesmerizing tapestry of reds, oranges, and yellows, making these neighboring states an idyllic haven for nature lovers and leaf-peepers alike. Following this itinerary, you’ll get to savor the sights, flavors, and cozy moments that define the magic of autumn in this enchanting corner of New England.


Why this itinerary

There are countless amazing places to go leaf peeping in the US outside of New Hampshire and Vermont – upstate New York, Maine, Michigan, Colorado, Tennessee, etc. all come to mind just to start – and this itinerary is by no means meant to declare that experiencing fall foliage along this route is superior to other fall foliage destinations!

However, what this itinerary does offer is an incredible cross-section of quintessential New England autumn experiences perfect for a first-timer to the area. From historic and charming small towns, to sugar in multiple forms spanning apple cider, maple syrup, maple creemees and donuts, to the vibrant changing colors, this itinerary feels manageable and only totals 11.5 hours of driving over four days of travel despite being packed with gems.

Yep, that’s right – this itinerary is PTO-friendly, even from the West Coast! It only requires two days off work when paired with a weekend, and because the itinerary originates with a flight into Boston, West Coasters may find efficient redeye flight options with lie-flat seats that allow one to sleep on the way there and hit the ground running in the morning upon landing.

What does this itinerary miss?

If there’s one thing I want to stress after reading through the many comments left on my social media videos about this itinerary, it’s that no single itinerary is going to cover every single place that could be incredible to see or activity that’s amazing to do along a given route, nor can it cover every possible permutation of a route!

This is just the itinerary I planned and executed after a lot of research and taking into consideration the time constraints (remember, the goal was PTO-friendly!). After executing this itinerary, I feel I nailed it – I absolutely loved the stops and the flow of the trip, which is why I’m sharing it.

That being said, if I had more time or came back to this general area again and wanted to explore new spots, I would likely try to work in some time in western Maine as well as Vermont’s Northeast Kingdom. These areas are more rural and thus not as great for an efficiency-optimized itinerary that also prioritizes fun stops in addition to scenic landscapes, but the landscapes in these two areas look unreal – photographer catnip, if you will.

Without affecting the structure of the itinerary, you could also try to squeeze in a ride on the Conway Scenic Railroad on day 1 – we decided against it, instead using a couple of hours that day for a personal stop (visiting Lance’s boarding school!). Without that constraint, I would’ve loved to try it as it’s right on the way.

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! For the areas this itinerary covers, early- to mid-October tends to be the sweet spot.

Source: SmokyMountains.com

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.

A word on safety and etiquette

Understand that fall foliage is a wonderful time in New England, but the concentration of tourists packed in trying to catch the fleeting foliage spanning such a short window of time can cause stress on local populations.

First and foremost, be an alert driver. I loved driving the back roads that got us from one stop to another, but thank goodness I am as attentive a driver as I am – at one point, two younger kids came speeding on ATVs across the road in front of me out of nowhere (no marked trail, no houses nearby, out of a dense forest). I slammed on my brakes and very narrowly avoided disaster, but it rattled me for the rest of the day. Had I not been paying extremely close attention despite being on deserted back roads with no other cars or people around, that encounter could have ended tragically.

Likewise, alertness should carry through to any stops you make to snap some shots or take in the sights. Don’t park in the middle of the road, no matter how deserted that road seems. It takes the tiniest bit of effort to be conscientious of others and pull over to the side of the road before hopping out.

Lastly, there is a popular spot that has long been heralded as Vermont’s most photographed private residence. I will not name it myself for reasons I describe in a moment, but this is a farm whose image many people consider synonymous with fall. While it’s been a photography haven for many years, it seems that with farm ownership changes and bad behavior on the part of a small number of visitors, the farm’s current owners and the neighbors around it have grown less and less thrilled with the tourism it brings in every fall.

As such, for the 2023 fall foliage season, they are shutting down non-resident access to the neighborhood for three weeks. Respect their wishes. I visited last year fully respecting that it’s a private residence and stayed on the public road (where only one other person was there photographing the farm at the time, though I believe it can get packed) hence the one-second clip you see of it in one of my fall foliage itinerary video on social media, but the rules are different this year and you should respect the rules as they currently stand. 

The itinerary

Day 1

Fly into Boston on a redeye if you’re coming from the West Coast or the first morning flight in if you’re coming from the East Coast. If you’re coming from the East Coast, you can also consider flying into a smaller regional airport like MHT, though you’d likely need to switch these days around to suit a different starting point. I liked flying into BOS because there were nonstop options with lie-flat seats from LAX, plus a large selection of rental car agencies with ample supply.

After you pick up your rental car, head to Smolak Farms or Russell Orchards for a breakfast of apple cider donuts to launch you right into a festive fall vibe. Smolak Farms opens at 7 a.m. whereas Russell Orchards opens at 9 a.m., so if your flight lands early in the morning like ours, Smolak will be your best bet. After 9 a.m., it’s up to you which you want to prioritize!

The bulk of your first day is going to be dedicated to the stunning 34.5-mile-long Kancamagus Highway in New Hampshire. We started west around Lincoln, NH and headed east toward Conway, but you could just as easily do it in the other direction.

Kancamagus Highway is such a special stretch to start off the trip; it’s lined with amazing views of the sprawling tree-covered White Mountains, state parks, hikes and more. This is very much a choose-your-own-adventure type of day. As you wind the curves of this scenic byway, you’ll see various pockets of people pulling over into parking areas for view after view. Pull over with the crowds or find your own nooks, and spend a few minutes or a few hours at each stop – the day is yours and Kancamagus’s alone. 

Once you reach the end of Kancamagus, drive up to Omni Mount Washington Resort to catch sunset with a drink on the wraparound porch and finish up with dinner in the White Mountains area. We ate at the Inn at Thorn Hill and loved their Bee’s Knees cocktails.

Where to Stay

You could get a room at either the Omni Mount Washington or Inn at Thorn Hill stops, but there are a number of other cute inns in the White Mountains area as well. We stayed at a friend’s house along the northern edge of the White Mountains ourselves.

Day 2

Wake up and make the short drive across to Vermont! We started our day in Danville, Vermont thanks to some specialized research on my part – I really wanted to find a local fall festival that lined up with our travel dates. I grew up with these types of festivals in Ithaca, NY (our local fall festival was the Apple Fest!) and they’re such a joy!

Here’s an example of a resource to find a fall festival that might work for your dates (I found the site where that calendar lives, Jeff Foliage, to be a phenomenal niche resource while planning).

After visiting Danville’s Autumn on the Green festival, we hopped around nearby beautiful small towns in the area. Peacham in particular was lovely – the owner at the small Peacham Cafe was so welcoming despite his entire staff being out sick that day.

After getting your fall festivaling in, stop by Burtt’s Apple Orchards for apple or pear picking, a corn maze and more apple cider donuts.

We next made our way to our resort for the night which is where we also had dinner, but you could venture into the town of Stowe for a number of local dinner options there instead.

Where to Stay

We spent the second night in Stowe at the Lodge at Spruce Peak and the room we booked might have one of the most beautiful fall foliage hotel room views you can get in Vermont!

While the Lodge at Spruce Peak itself was nice enough (if not cut from the same cloth as many large cookie-cutter ski resorts), this room’s view made our stay.

The keyword to look out for when booking is the Alpine view; I booked us in an Alpine Studio which features a guaranteed view onto the mountain and trees, whereas the lower room categories either don’t have mountain views or only have partial views. We paid $760 for the night we stayed.

Day 3

Another standout feature of a stay at the Lodge at Spruce Peak is the gondola that leaves from just outside the hotel. This short gondola ride connects to another gondola that goes up through the peak’s fall colors for another vantage point of the changing leaves!

After checkout, head to Cold Hollow Cider Mill. Warning – be prepared for crowds and lines, so if it’s not important to you to make this popular stop, it’s okay to skip it (I won’t tell!). There are literal tour buses that stop here to give an idea of the size of the crowds! If you do decide to go, Cold Hollow offers a back room with self-serve cider tasting, fresh cider donuts up front, and a hard cider tasting room next door.

Next make your way to Morse Farm Sugarworks. Here you can learn about how maple syrup is made followed by a maple syrup tasting of the different grades they sell. This is a great spot to buy some maple syrup to bring home!

And as if your day hasn’t been filled with enough sugar already, Bragg Farm Sugarhouse is the next stop I recommend. Here you have to get a maple creemee, an ice-cream dessert that resembles soft-serve and is a must-have treat while you’re on this road trip. While I loved our stop at Bragg Farm, you also have the option to enjoy a maple creemee at Morse Farm (the last stop) if you prefer to condense the itinerary a bit and skip this stop.

Make your way to Woodstock, Vermont where you can start winding down the night starting with a cocktail at Au Comptoir, followed by dinner at the Worthy Kitchen for a more casual option or The Prince & The Pauper for a more upscale dining experience.

Where to Stay

Our third night was spent at an inn that has been on my bucket list for ages, and if you’re planning a Vermont fall foliage road trip, it’s going to be impossible to escape hearing about it: The Woodstock Inn & Resort in Woodstock, Vermont.

When booking, any “Tavern” room will be in the Tavern wing, also known as the more luxurious wing of the resort. I booked a Tavern King which looked onto the back lawn and featured a fireplace (or a heated animation of one). The bathroom was tiny but I loved the classic New England room decor. We paid $900 for our room for the night.

The actual resort itself is quite large at 142 rooms and suites despite its quaint facade, and you get a better idea of its size from the back lawn where you can see how the resort complex wraps around.

The inn’s location is one of its biggest selling points: you’re right in the village, just steps from so much of what Woodstock has to offer.

Day 4

The home stretch! On this last day, your return flight (or drive) will determine how much time you have to explore Woodstock further. This is a great time to visit the famous covered bridges in Woodstock and surrounding areas, walk the village, stop in local flannel shops, and drive the picturesque back roads. 

From Woodstock, you’re about a 2.5-hour drive to BOS airport. Ensure to budget enough time before your flight to return your rental car and check your bag if you bought liquids along the way (such as maple syrup)!

Pro tips: finding one-night hotel stays

Part of the fun of a road trip is keeping things moving, but because the window for fall foliage usually spans such a short period of time, many hotels understandably institute minimum stays greater than one night.

I like to lovingly call this the Fall Foliage 2-3 Struggle: during the 2-3 weeks of peak leaf-peeping tourism, a lot of resorts institute 2-3 night minimum stays in addition to hiking their rates 2-3x. Minimum stays are not our friend on itineraries like this!

To work around those multiple-night minimums, I have two main tips:

First, when you search for rooms, many inns in the area have availability calendars that look like this: 

In this example for a random inn for next month in Vermont, you’ll see that three of their rooms have a single night between bookings where they’re not booked. Once you have this information, call up the inn or hotel and see if they’re willing to manually quote you a rate for that one night. This is a win-win for you and the property: you get a one-night booking and they sell a room their online system might otherwise not allow you to book due to the minimum stay requirements.

Second, don’t be married to the idea that a four-day weekend means Thursday to Sunday; a Saturday to Tuesday trip, which is what we did, is still just two days off work and you’re less likely to run into minimums on Sunday and Monday nights.

And last, a bonus tip for those of you planning for next year: most popular inns and hotels start booking out 11-12 months in advance, but they don’t necessarily have the minimum stay requirements for bookings made that far in advance. If you start looking soon for the 2024 season, you might be able to book single nights. I personally had success with this in 2021 when I was booking our 2022 fall foliage trip!

In Conclusion

Over the span of just four days, this leaf-peeping road trip through New Hampshire and Vermont immerses you in the kaleidoscope of nature’s finest hues, driving along scenic byways, savoring apple- and maple-syrup flavored treats, and relishing the crisp fall air. From the rugged beauty of the White Mountains to the quaint charm of Vermont’s covered bridges, this trip touches on so much of what makes people think of New England when they envision a storybook autumn trip. May your adventures here be as colorful as the foliage that blankets these enchanting states!

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