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September 21, 2020

Charming New England Towns To Visit This Fall

Fall In New England

New England is pretty special in fall, it is a truly magical time of year. There are so many fun things to do each fall and New England truly embraces the fall season. Although peak foliage varies from year to year (because of weather) your best bet for visiting New England during peak fall foliage in the first and second week in October. Check out this fall foliage map to plan out the perfect time to see these charming town in all of their autumnal glory! But there are so many great towns in New England, where should you visit?

The Most Charming New England Towns To Visit
This Fall
 [show]
  • Massachusetts: 
    • 2020 Specific Information: 
    • Salem – 
      • Read Next:
    • Concord – 
      • Read Next:
    • Mohawk Trail – 
    • Stockbridge – 
  • Maine:
    • 2020 Specific Info: 
    • Camden, Camden State Park – 
      • Read Next:
    • Bar Harbor/Acadia National Park – 
      • 2020 Specific Info For Acadia National Park: 
      • Bonus:
      • Read Next:
  • New Hampshire:
    • 2020 Specific Information: 
    • Dixville Notch State Park – 
    • North Conway/Lincoln – 
    • White Mountains – 
      • Read Next:
  • Vermont: 
    • 2020 Specific Information: 
    • Woodstock – 
    • Stowe – 
      • Read Next:
    • Smugglers Notch – 
    • Upstate NY: 
    • 2020 Specific Information: 
    • Adirondacks – 
    • Letchworth State Park – 
    • Hudson Valley/Sleepy Hollow – 
      • Read Next:
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Massachusetts: 

2021 Information: 

  • Effective August 23, 2021, the City of Salem requires masks to be worn in all indoor public areas. Salem’s mask requirement is currently in place through November 13 pending public health data.

Salem – 

Fall in New England

Salem, Massachusetts is pretty synonymous with October/Fall/Halloween and for good reason. There are so many fun things to do in this charming New England town during the Halloween season.

Although this year the famous Salem Haunted Happenings is canceled there are still tons of things to do! Check out some historical sites from the Salem Witch Trials, get a hand carved wand from Wynott’s Wands, take a guided cemetery tour, or have some drinks at Far From The Tree Cider. Check out the suggestions below for more specifics on Salem. 

Read Next:

Salem Fall Bucketlist, All The Best History Spots In Salem, 9 Things To Know Before Visiting Salem in Oct, Hocus Pocus Self-Guided Tour, Perfect Fall Day In Salem

Concord – 

Concord, Massachusetts is such a quintessential enchanting New England town with tons of history! Not only can you check out Revolutionary War sites, but Concord is also a literary nerds dreams come true. See where the 2019 Little Women was filmed and don’t forget to grab a bite at the Colonial Inn.

Take a walk through the gorgeous fall foliage at Minute Man National Park and check out Old North Bridge where the infamous first shot of the revolution was fired. You can’t go wrong in Concord in the fall. 

Read Next:

One Day In Concord, MA, The Best History Spots In Concord

Mohawk Trail – 

The Mohawk Trail in Western Massachusetts was actually the first scenic route in all of New England and officially opened in 1914. It boasts an incredible 50,000 acres of state forest and parks. Historically speaking, the Mohawk Trail is named after the footpath created by Native Americans that connected the Connecticut and Hudson River valleys. This land belonged to the Pocumtuck and the Mohawk.

But that’s not the only historical claim to fame as this is the route Benedict Arnold took when marching to Fort Ticonderoga in New York. That was before the whole traitor thing when he was recruiting troops on his way from Boston. You can actually still hike part of the original footpath within Mohawk Trail State Forest.

Stockbridge – 

Maybe you’ve never heard of Stockbridge, MA but chances are if you are a Norman Rockwell fan, you have! This is the home of the iconic New England holiday scene, immortalized by Norman Rockwell in his work, ‘Main St., Stockbridge’.

Visit the Norman Rockwell Museum while in town, enjoy the warm autumn sunshine on a park bench, or grab a bite to eat at Once Upon A Table. Enjoy the many charming little gift shops on Main St. and Elm St while watching the leaves fall and sipping on a hot cider. You can experience your very own autumn Rockwell moment in Stockbridge! 

Maine:

Camden, Camden State Park – 

Camden, Maine is charming at any time of year but there is something special about this town in fall. It’s actually been included on several famous (ahem Froders and Travel and Leisure) lists of the best places to visit in New England in fall.

While a scenic walk with a coffee in hand from Owl & Turtle Bookshop is a must, there are more unique ways to view the foliage. Camden is known as the place where the mountains meet the seas, so it makes sense that you can view the colorful leaves from the top of Mount Battie. You can also take that coffee to the harbor and enjoy watching the boats with the backdrop of gorgeous fall foliage. 

Read Next:

11 Amazing Things To Do In Camden, ME

Bar Harbor/Acadia National Park – 

The first thing you should know is that fall is an incredibly popular time of year to visit Acadia and you need to book accommodations early. Fall foliage usually hits peak around mid-October as the park becomes draped in vivid hues of oranges and yellows.

The leaves are stunning, and the unique coastal location of Acadia really creates some autumn magic! It’s important to keep in mind that although Bar Harbor is incredibly charming most restaurants and shops run on seasonal schedules.

Bonus Acadia National Park:

From Oct 7 to March 6 each year Cadillac Mountain in Acadia National Park is the first place to see the sunrise in the United States. That makes taking in a sunrise at Cadillac Mountain pretty special. Be aware that almost everyone goes to Cadillac Mountain for sunrise. For that reason, you now need to make a reservation to take in a Cadillac Mountain sunrise you can do that here. Read the link below for more information of sunrise at Acadia National Park. 

Read Next:

Best Sunrise Spots At Acadia, 10 Can’t Miss Dog Friendly Hikes At Acadia National Park, Camping At Acadia: The Complete Guide, Is Acadia National Park Dog Friendly?

New Hampshire:

Dixville Notch State Park – 

The best way to see fall foliage in New Hampshire is to get outdoors and hike! Check out the dog friendly Table Rock Trail, it’s dog friendly, rated moderate, and 1.5 miles. The Dixville Flume is also really popular and is sure to offer those gorgeous fall colors. Grab lunch at the Black Bear Tavern and enjoy the falling leaves as you stroll to a beautiful waterfall. 

North Conway/Lincoln – 

You can’t go wrong in New Hampshire in the fall but one of the most popular things to do is take a scenic fall ride on the Conway Scenic Railroad. Enjoy the foliage of the Mount Washington Valley and Crawford Notch in the comfort on a railcar. You can book your trip here and all passengers are required to wear masks in 2020.

Or drive yourself on the  Mount Washington Auto Road, it costs $35, but you get to see all those stunning fall colors from the top of Mount Washington. After all, due to its remarkable location, weather, and history, the Mt. Washington Auto Road is unlike any other driving experience in the Eastern United States.

Speaking of scenic drives, do NOT miss out on taking the Kancamagus (the Kanc). This 34.5-mile scenic drive along NH’s Rt. 112 in Northern New Hampshire is well known as one of the best Fall Foliage viewing areas in the country.

The Kancamagus Highway is now designated an American Scenic Byway for its rich history, aesthetic beauty, and culture. I’ve driven the Kanc in the autumn sunshine, rain, and even early autumn snow and can tell you firsthand, no matter what the weather, it’s gorgeous!! 

White Mountains – 

The White Mountains and Franconia Notch State Park are some of my favorite places to visit during the fall season. There is just so much to do and so many gorgeous hikes to take!

Head to Franconia Notch State Park and check out the Flume Gorge and Artists Bluff Trail. Or if you are looking for something a little more challenging head to the Welch & Dickey trail for stunning fall foliage and summiting two mountains! Check out the link below for more specifics. 

Read Next:

The Best Dog Friendly Hikes In New Hampshire

Vermont: 

Woodstock – 

Woodstock, Vermont is exactly what you want a charming New England town to be. Masks are now required in the village but enjoy a brisk walk through Woodstock’s village. Take in that extra dose of charm thanks to the vibrant colors of fall foliage. For even more charm head to Sugarbush Farms and check out their animals, sugar house, and an unbelievably enchanting chapel in the woods. The drive itself is worth it. 

Stowe – 

Fall

Stowe, Vermont is one of my all-time favorite places to visit in the fall. To get the best view of all those reds, oranges, and yellows take a great scenic drive on Stowe Mountain Toll Road. It costs $33 for two people and the dogs and they take both cash and cards. Dogs are allowed at the top parking lots as long as they are on a lead. If you have enough time check out the Chin Hike to the tallest point in Vermont. The trail is 1.5 miles and takes about 90 minutes to complete. 

Fall

Take a stroll through downtown and check out Shaw’s General Store before heading out of town make sure to stop at Cold Hollow Cider Mill. They have THE best cider donuts, but also check out their warm cider, cider slushies, and the dutch apple pie. So yummy! 

Read Next:

One Day In Stowe, Vermont

Smugglers Notch – 

Fall

All of those famous photos that you’ve seen of Smugglers Notch in fall – yep, that’s right outside of Stowe! Most of the notch is located in Mt. Mansfield State Forest. It’s a gorgeous drive and one that you absolutely need to take in the fall. 

Upstate NY: 

Adirondacks – 

There is so much to do in the Adirondacks in fall. Take a scenic drive from Keene through Lake Placid and onto Saranac Lake. Lake Placid is known for having some of the best fall foliage around and you’ll drive right through. Or hike Bald Mountain, which is only 2 miles, rated moderate, and known for beautiful fall colors. 

Letchworth State Park – 

Letchworth State Park, renowned as the “Grand Canyon of the East,” is one of the most scenically magnificent areas in the eastern U.S. Just add in those gorgeous fall colors and you’ve got a perfect autumn day! 

Hudson Valley/Sleepy Hollow – 

Fall

Is there any place that screams fall/Halloween more than Sleepy Hollow, NY (maybe Salem, MA)? Although many of the normal Washington Irving attractions that draw people to Sleepy Hollow have been canceled this year there is still plenty to see!

The best time to visit the Hudson Valley for fall color in mid-October, most years. Tour the Old Dutch Church Cemetery to see some of the inspiration behind The Legend of Sleepy Hollow. Listen carefully as someone drives over the Headless Horseman bridge and you can hear the hoofbeats of the Hessian soldier’s horse. Check out the link below for more ideas for your visit to Sleepy Hollow, NY. 

Read Next:

One Day In Sleepy Hollow, New York

New England really is magical in the fall and worth a visit! Even if you only take a drives through these beautiful states, you really won’t regret it! Have you been to New England in fall? Which location was your favorite?

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Posted In: New England · Tagged: Fall, Fall Colors, Fall In New England, Fall Travel, Most Charming Towns, New England, Perfect Fall Trip

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Hi! I'm Vanessa, a 30 something, sunset chasing traveler. I'm here to inspire you to travel wherever, whenever, and with whoever you can. My Huskies, Loki and Freya are usually along for the ride. I have a soul that likes to wander, a desire to experience the unknown, and a curiousity to discover things off the beaten path. I hope you'll stick around for awhile!

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I lived in New England for 7 years, and every Octo I lived in New England for 7 years, and every October I watched people make the same mistakes.

Wrong direction. Too many towns. A gate closed 3 days before arrival. And that one farm photo everyone swears you can still get…except you can’t.

Every year I also had a handful of visitors who wanted to see this town or go to that festival in the fall, and I’ve explored SO many of them. Fall was my favorite in New England

So I made the version I’d actually hand a friend or tell them over coffee, because that’s why I do here 🍁🧡

🍁 A six-state clockwise route
🍁 7-day + 10–14 day itineraries
🍁 2026 closures + reservation windows in one place
🍁 Dog-friendly stops (and the four that absolutely are not)
🍁 What to do when your trip slips a week and the mountains have already moved on

🍁✨Plus a Google Map companion with every stop, because “no service” and “where the hell are we?” tend to arrive together.

The Ultimate New England Fall Road Trip Guide is 19 pages of all of the best New England has to offer in the fall. 

🍁🍂 Comment LEAVES and I’ll send you the direct link.
It’s the most hauntingly beautiful thing in the Ro It’s the most hauntingly beautiful thing in the Rockies and it’s happening right now.

Everyone goes to Moraine Park for rut, and it’s great, and there are 300 cars. This was the top of Trail Ridge Road, above treeline, one bull, his harem, and us.

For about a month every fall, the bulls barely eat or sleep and lose up to a fifth of their body weight holding their cows together and warning off every other bull in earshot. The sound carries for miles.

If you go: Trail Ridge Road closes for the season in mid-to-late October, so the rut window up top is short. 

In Yellowstone, head to Mammoth Village to see the elk (I’m hoping to get back this fall) 

And in Grand Teton, just keeps your eyes open 👁️

🚫 Stay a 75 feet minimum. This is the one month they’re looking for a fight.

✨Save this for your trip to the Rockies from mid-September to early October ✨
105 miles of overlooks on Skyline Drive…gorgeous i 105 miles of overlooks on Skyline Drive…gorgeous in fall! 🍁🍂🍁

I made a joke in a post during National Park week that Shenandoah was really just a great scenic drive. While I WAS joking, I would see the same thing year after year. Every October it’s the same: pull in, take the photo, pull out, repeat. 

What you’re driving past is over 500 miles of trail, and your dog is allowed on all but about 20 of them. After Acadia, it’s got some of the best dog-trail access on the East Coast.

The catch: the two trails you’ve heard of, Dark Hollow Falls and Stony Man, are on the short no-dogs list. So skip them. 

Rose River gets you a waterfall in under four miles, Hawksbill gets you the highest point in the park in 1.5, and both take the dog.

I lived an hour from this park for 5 years, and I’m telling you, while it’s totally ok if you only drive the Skyline Drive, you’re missing out in some of the true beauty of Shenandoah if you don’t take a short hike. 

Peak on the Drive usually runs mid-to-late October, north end first. Go on a weekday. Bring the dog 👌🏻

🍁🍂 Save this for your fall Shenandoah trip 🍂🍁
Last summer, someone visiting for a few days would Last summer, someone visiting for a few days would find out we were on the island for the season and ask the same thing: if I only have time for one trail, which one?

6 months. Same answer every time. And it’s probably not the one you would think. Here’s the thing, Acadia’s most popular trails are phenomenal, and I kind of understand why every single list you see has the same 5 hikes, BUT, personally I don’t like waiting in a line to hike. 

So my answer: 

⛴️⚓️ Ship Harbor - It’s on the quiet side past Southwest Harbor, a 1.3-mile (so perfect for every age and fitness level) figure-eight that starts in spruce forest and opens onto pink granite, tide pools, and the actual Atlantic. No scramble, no reservation, no iron rungs. Flat enough that everyone in your group can do it. Dogs on leash are welcome. Go at low tide if you can swing it, because the tide pools are 👌🏻

✨ Save this for your Acadia trip ✨
Hi, I’m Vanessa. I turned 40 this year (Millennial Hi, I’m Vanessa. I turned 40 this year (Millennial 90’s kid here), I have 3 dogs, and I live in a 40-foot travel trailer named Betty with a man I met in the woods in 2022.

We’ve been full-time on the road since 2023, Idaho is technically home base at the moment, and I’ve been to 22 of the 63 national parks with 41 to go.

What you get here: honest park guides, dog-friendly trails that are actually dog friendly. No hidden gems that turn out to be closed on Tuesdays. No telling you to quit your job.

Mostly I just want you to have a better trip than the one you’d have without me.

Glad you’re here 💚

Tell me where you’re headed next, I probably have opinions 😉
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