New England Fall Road Trip 2021 – The Ultimate Guide

The most vibrant of all seasons, and easily my favorite of all is Fall! For the last 9 years, I’ve watched the colors turn in complete awe – each time feeling just as fascinated as I did the first year! Speaking of firsts, 2021 was the first year when I decided to commit to my love for the season, and took a week-long fall road trip across New England. And I’m here to share everything with you – what I did, places I loved, and things I wanted to do but didn’t have time for.

New England fall foliage update for 2021:

Peak foliage is approaching in the Stowe area of Vermont this week (Oct 11 – Oct 15 2021). Most of the Franconia area in New Hampshire has a lot of colors showing, but you can probably wait a couple more days before getting there (Oct 14 – Oct 18 2021).
Southern parts of both Vermont and New Hampshire should start showing peak colors over the next week.

Taftsville covered bridge, Vermont
Taftsville covered bridge, Vermont

How to plan your New England Fall Road Trip

Timing your New England fall road trip

With the peak fall foliage time changing every year, and the high demand for accommodations during the season, it can get a bit overwhelming to plan a New England fall road trip. Here’s a strategy I recommend

  • Book accommodations that can be canceled/rescheduled either for free or at a small cost
  • Consistently check these weekly foliage reports (these are more accurate than the foliage tracker maps that are generally based on past averages)
  • Err on the side of slightly early rather than slightly late, so that you can can
    • extend your trip or revisit if you choose to do so (better than having to wait a whole year)
    • edit colors in your pictures during post processing (easier than having to photoshop leaves onto trees)

Staying true to my strategy, I was in Vermont and New Hampshire at least one week before peak colors this year, but I still had a fantastic time!

Planning the route for your New England fall road trip

Although I wouldn’t rely on this New England foliage tracker map for the exact dates, I found it extremely helpful to estimate when and how to plan my fall road trip.

new england fall foliage tracker map

As you can tell from the image above, the colors start to show from north-west to south-east, gradually changing from mid September to end of October.

So, if you’re chasing peak foliage across New England, your best bet is to

  • Start at the northern parts of Vermont around Stowe
  • Then move east to the White Mountain region in New Hampshire
  • Travel south towards the Monadnock region in New Hampshire
  • Then back into southern Vermont (Woodstock) and western Massachusetts (Berkshires)

If you have some extra time, you could also consider visiting Acadia National Park in Maine. Although, if it were up to me, I’d just spend more time in Vermont!

What to pack for your New England Fall Road Trip

With the end of summer, we typically see a lot of rain and chilly nights during the weeks of September rolling into October. That means you’ll want to pack your

  • rain jackets
  • umbrellas
  • warm socks
  • boots
  • sweaters
  • trench coats
  • scarves

That said, you should look to dress in layers so you’re prepared for variations in temperature as well as variations in your physical activity through the day.

New England Fall road trip vermont
Stopped at a random scenic spot on my way

Other absolute musts:

  • snacks and water – what’s a road trip without snacks?
  • a camera (or phone) and some extra batteries/charger
    • come prepared with an external hard disk to back up & clear your camera memory if you plan to capture a lot of photos/videos – you’ll most definitely want to!
  • a fun playlist, audiobooks, or stories for the journey

New England Fall Road Trip Itinerary

If you’re not from New England, Boston is the recommended airport to fly into before setting off on the drive. Being from Boston, I obviously started my journey from Boston as well!

Also read: 10 Most Instagram-worthy places in Boston

Day 1 – Boston, MA to Stowe, VT

Montpellier

Montpellier Skyline - new england fall road trip Vermont
Montpellier Skyline

Start early, and drive 3 hours to Montpellier – the capital of Vermont. I made a quick stop here, to check out the skyline of Montpellier, and Vermont State House.

Other things to do at Montpellier:

  • Visit Bragg Farm Sugar House & Gift Shop
  • Check out the Coburn covered bridge

Waterbury

Home to one of Vermont’s most popular tourist sites – the Ben & Jerry’s Factory – Waterbury is a fun stop to make for a couple of hours. Things to do in Waterbury include

  • Visit Ben & Jerry’s Factory (scoop shop open, but tours closed in 2021)
  • Have a coffee and buy chocolates at Lake Champlain Chocolates
  • Check out Ziemke Glassblowing Studio
  • Buy Maple Candy and Cider at Cold Hollow Cider Mill
Woodstock Inn, Woodstock Vermont

Drive to Stowe along Scenic Route 100

Also known as the Green Mountain Byway or Vermont’s Main Street, you’ll already be on this byway as you’re stopping by all the spots to check out in Waterbury. This is one of New England’s most scenic routes!

Arrive at Stowe

Depending on how you feel, you can drive along one of Stowe’s scenic drives, or relax for the evening with a beer from The Alchemist.

Stowe Vermont during fall
Iconic View of Stowe

Day 2 – Stowe, Vermont

Gondola Skyride

Start the day with the Scenic Gondola Skyride up Mt. Mansfield to get an elevated view of all the beautiful and vibrant foliage colors!

Hike to Bingham Falls

Hike the easy-to-moderate Bingham Falls trail. Note: although the trail is short and shouldn’t take more than 30 minutes round-trip, be prepared for a bit of a steep climb down towards the view-point.

Girl sitting in front of Bingham Falls New England during fall at Stowe Vermont
Bingham Falls

Downtown Stowe

Check out downtown Stowe. My favorite spots here are

  • Laughing Moon Chocolates
  • Mac’s Market – where you can load-up on
    • local cheese – I recommend trying the Cabot cheese Pepper Jack)
    • local Vermont wines – I bought the 2016 Frontenac Gris from Fresh Tracks Farm, an old favorite of mine
  • Salon Salon parking lot for a view of Stowe Community Church – one of New England’s most photographed church
new england fall road trip - stowe community church, vermont
Stowe Community Church – one of New England’s most photographed church

Hike to Moss Glen Falls

That’s right! Two waterfall hikes in one day!

Go on another easy hike to Moss Glen Falls. Well-maintained and mostly flat with a short climb up to the view-point, this trail felt a lot easier than the Bingham Falls trail. However, if you only have time for one of the two, I recommend picking Bingham Falls.

moss glen falls stowe vermont during Fall
Moss Glen Falls

Day 3 – Stowe, VT to Franconia, NH

Smugglers’ Notch

Drive along the curved roads of Smugglers’ Notch for the best views of foliage cover along the streets. Going here early in the morning will make it easier to find spots to park off the driving lane and shoot on the street without too many interruptions from other vehicles or leaf peepers.

new england fall road trip - foliage on curved roads at smugglers notch stowe vermont
Smugglers’ Notch

Pro tip: There are sharp (blind) curves along the road with some steep inclines and narrow patches – so, be alert while driving through Smugglers’ Notch!

Zip Line

Do a zip line tour with either Ziptour Adventure (open June – October and touted to be the most exhilarating zip line) or Arbortrek Canopy Adventures (rated among best 10 zip lines in USA, open all year round).

I did the Arbortrek zip line tour, a 2.5 hour guided tour with 8 zip lines and 2 rappels. This was my first zip lining experience and it was nothing short of amazing, thanks to guides Cora & Kris!

Hike Owls Head Trail – Groton State Forest

Start your ~2 hour eastward drive towards New Hampshire, but stop on the way at Groton State Forest to hike up Owls Head Mountain for a sunset view of the foliage and Kettle Pond from an elevation. This is a 3.2 mile hike (roundtrip) and is rated as moderate.

Vermont Kettle pond view from Owls head mountain with New England fall foliage
Owls Head Mountain (Image Credit: jeff-foliage.com)

I unfortunately had to cancel this hike last week as I had a sore shoulder and wanted to quickly finish my drive up to Franconia, NH so I could check-in to my next accommodation and get some rest. I might just decide drive up there this week though, who knows!

Arrive at Franconia, New Hampshire

I drew up a lovely warm bath in a jet tub and relaxed with some cheese, wine and chocolates that I bought at Stowe. The warm water and some sleep thankfully helped me feel better soon enough!

Always go a little extra when it comes to self care!

Also read: Best Fall Photoshoot Locations

Day 4 – Franconia, New Hampshire

Artists Bluff

The Artists Bluff trail starts opposite the Echo Lake Beach parking lot, and is a short but steep hike.

The view? One of the best I’ve ever seen! You’ll get to see Echo lake surrounded by peaks and valleys full of vibrant colors! On a day when it’s not windy, you’ll also see crisp reflections of the mountain in the lake, and maybe even the early morning fog.

Artists Bluff Franconia New Hampshire
Artists Bluff – one of the best views I’ve seen!

Although many people complain about the highway along the lake, I think it adds to the view – telling the story of human interaction with nature, the story of the ancient meeting the modern. And the fact that I have to take that highway back to Boston gives me the warm feeling of looking at my way back home!

I recommend going here early in the morning so the sunlight isn’t too harsh on the face of the mountains. This place is popular during sunset and can get very crowded, especially during summer and fall seasons.

Flume Gorge Trail

The Flume Gorge trail is perfect for people of all ages. With covered bridges, natural rock formations, waterfalls, and colorful foliage all around, this well-maintained trail is great to walk around for a couple of hours.

Covered Bridge at Flume Gorge Franconia New Hampshire
Covered Bridge at Flume Gorge

Come prepared to share stories with your group as you walk, admire the works of nature, and stop for photo-ops along the way!

One of many falling water displays at Flume Gorge Franconia New Hampshire
One of many falling water displays at Flume Gorge

Day 5 – Franconia, NH to Woodstock, VT

All About Trains

Depending on your interest in photographing railroads and trains or taking a scenic ride on one, here are some options for you to consider:

new england fall road trip - foliage and train tracks
My love for nature, travel, colors, and pretty clothes – all in one!

Pro Tip: If you’re planning a photoshoot at these railroads, make sure to check the links above for schedules before you set out – some of these trains are super infrequent!

Also read: Best Fall Photoshoot Locations

After a day of train adventures, drive back to Vermont into the Woodstock region for some barn and farm fun!

Day 6 & 7- Woodstock & Killington, Vermont

I probably felt this way each day at every single place, but let me tell you that the Woodstock region is one of the best places to be when on a leaf peeping adventure. This is where you’ll find the cutest rural vibes – quiet towns, little roads connecting them, covered bridges, farms, and best of all, farm animals!

Walking along Woodstock during Fall
Walking along Woodstock during Fall

The browns and reds of the bridges and farms go so perfectly with the theme of autumn, making the entire place come alive with just the colors we’re looking for!

Walking around the Woodstock village will give you plenty of opportunity to enjoy the fall foliage set against homes decorated for the season. If you’re like me and like having a list of places to guide you through your exploring, I’ve got just what you need below.

Middle Covered Bridge, Woodstock, Vermont

Woodstock region

  • Quechee Covered Bridge (also check out Simon Pearce glassblowing while here)
  • Taftsville Covered Bridge
  • Sugarbush Farm (gorgeous elevated view of foliage)
  • Maple Grove Farm
  • Sleepy Hollow Farm (expect some crowds here, thanks to this farm’s star status on Instagram!)
cows grazing at Billings Farm during Fall in Vermont New England
Billings Farm, Vermont
  • Middle Covered Bridge
  • Woodstock Inn & Resort
  • Billings Farm & Museum
  • Jenne Road Farm

Also read: Best Fall Photoshoot Locations

Killington Region

  • Thundering Brook Falls Trail
  • Kent Pond
  • Texas Falls
  • Winslow Farms

I didn’t spend more than a day in this area. However, I did feel that two days here would be perfect to really cover all these places at a good pace without feeling rushed!

Girl dancing with Sleepy Hollow Farm Vermont in the background during Fall
Twirling in front of the most picturesque farm ever! (Sleepy Hollow Farm)

Aside: I’ve got a lot of questions about this skirt on Instagram, and decided to link it here for you in case you’re interested too!

Drive back to Boston

You might think the trip is over, but it actually isn’t! I have three more stops for you that are kind of on the way back to Boston. In my opinion, the views at these sports are totally worth the small, if at all, detour!

  • Weston, VT – The Old Mill Museum
  • Bennington, VT – Old First Church
  • Sudbury, MA – Wayside Inn Grist Mill

Also read: 10 Most Instagrammable places in Boston

That wraps up my epic New England Fall Road Trip itinerary. I hope this helps you plan trip – I’d love to hear from you if you found it helpful! If you have any questions, feel free to DM me on Instagram.

What are you most excited to see this Fall? Let me know in the comments below đŸ™‚

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