A New England Fall Bucket List: 5 Iconic Activities to Embrace the Season
As the summer months surrender to the refreshing, brisk days of fall, New England is transformed into an idyllic region that perfectly encapsulates the season.
Also, the October air has a kind of magic, the leaves are turning red, orange, and yellow, covering the scenery in a golden, warm glow.
The small towns, historic villages, and scenic countryside of the region is known for spring to life with the sights, sounds, and tastes of fall, making it a prime place to relish the season.
For many, autumn in New England isn’t just a season; it’s a beloved tradition, an opportunity to reconnect with nature, celebrate the harvest, and savor the simple pleasures.
Whether you’ve lived in New England your entire life, or you’re visiting for the first time, the region abounds with things to do that put the eye-popping peak of fall — and the fun — on full display.
Whether you’re taking a scenic drive through the rolling hills or enjoying fresh apple cider at a local orchard, there’s no shortage of ways to experience the season in all its glory.
Here, I’ll take you through five iconic fall activities every New England bucket list should include.
A piece of advice: These immersion experiences are ideal for exploring the fall-filled experiences found throughout the region that will help to encapsulate a perfect blend of nature, culture, and seasonal goodies.
1. Leaf Peeping on the Kancamagus Highway, New Hampshire
Nothing says fall in New England like leaf peeping, and few places are as spectacular for it as the Kancamagus Highway in New Hampshire.
Usually known only as “The Kanc,” this 34.5-miler passes through the White Mountain National Forest, providing some of the best views of fall foliage in the area.
The Kancamagus Highway is an American Scenic Byway, and for good reason.
The journey takes you through a diverse landscape of mountains, rivers, and forests, with plenty of opportunities to stop and enjoy the view.
There, you will discover scenic overlooks, hiking trails, and picnic spots where you can enjoy the season.
Don’t-Miss: The Sabbaday Falls, a waterfall surrounded by gorgeous fall colors, is a popular stop on the highway.
A short hike will take you through the falls, whose soothing roar of rushing water plays out against a colorful backdrop.
Best Time to Visit: Mid-September to early October to see the foliage at its peak.
2. Honey Pot Hill Orchards, Massachusetts﹣Apple Picking
No autumn in New England is complete without a visit to an apple orchard, and one of the best places to enjoy this quintessential fall activity is Honey Pot Hill Orchards in Stow, Massachusetts.
Honey Pot Hill has over 200 acres of apple trees and is the quintessential apple-picking experience suitable for families, couples, and adventurers on their own.
The orchard offers a diverse selection of apples, from popular favorites like McIntosh, Honeycrisp, and Cortland.
You can pick your own apples as you walk among the tree rows, filling your bag with the freshest fruit right from the branch.
Honey Pot Hill has more than just apple picking; you can go hayriding, through hedge mazes, and to the farm store, where you’ll be able to stockpile fresh cider, apple cider donuts, and other fall delicacies.
Must-See Highlight: Be sure to grab a taste of Honey Pot Hill’s famous apple cider donuts, hot out of the fryer and rich with the flavors of autumn.
Enjoy with a mug of warm apple cider for true fall bliss!
Best Time to Go: Late September to October, when the apple harvest is in peak.
3. Discovering the Covered Bridges of Vermont
Add to that Vermont’s famed covered bridges, and the fall is the perfect time to explore the historic structures.
They are also a symbol of the state’s rural heritage and a sought-after subject by photographers and history buffs: Vermont’s covered bridges, with their rustic wooden frames and scenic settings.
There are over 100 covered bridges in Vermont, each with its own story and architectural style.
Among the most notable are the US’s longest wooden bridge, the Cornish-Windsor Bridge, and the scenic views of the Quechee Gorge Bridge.
As you cruise the countryside, you’ll find that many of those bridges are in scenic spots, with colorful fall foliage, rolling hills, and babbling brooks.
Must-See Attraction: Woodstock Middle Bridge in Woodstock, Vt, is among the most-photographed covered bridges in the state.
Its idyllic location close to the town center, with classic New England charm, makes it one of the most must-see stops on your fall travels.
When to Go: Early to mid-October, when fall foliage is at peak.
4. Visiting the Deerfield Fair, New Hampshire
The Deerfield Fair in Deerfield, New Hampshire, one of the oldest agricultural fairs in the United States, began in 1876.
The quintessential fall fair is dedicated to New England’s agricultural traditions, with a blend of entertainment, food, and family-friendly fun.
It’s all part of the Deerfield Fair, which features the kind of classic fair attractions like livestock shows, horse pulls, and tractor exhibits.
The fair also includes a giant midway with rides and games, and plenty of food vendors serving everything from fried dough to apple pie.
One of the fair’s biggest attractions is the giant pumpkin contest, where local farmers compete to see who can grow the biggest pumpkin, a beloved fall spectacle.
Don’t-Miss Highlight: The giant pumpkin contest is not to be missed if you head to the Deerfield Fair; pumpkins on display can weigh upward of a thousand pounds.
It’s an exuberant, grand showcase of New England’s agricultural skills.
Best Time to Go: Late September through early October, when the fair is in full swing and the weather is ideal for outdoor activities.
5. A Scenic Train Ride on the Conway Scenic Railroad, New Hampshire
For an irresistible fall experience, head on board the Conway Scenic Railroad in North Conway, New Hampshire.
This scenic train ride through New Hampshire will allow you to experience the spectacular fall foliage in the White Mountains in a unique way, with routes taking you through some of the most beautiful scenery in New England.
The Conway Scenic Railroad has several different excursions from short roundtrips — scenic rides, short trips, lunch train, and a full-day excursion within the Crawford Notch.
Among the most well-known routes is the “Notch Train,” which runs through Crawford Notch, with cliffs, ravines, and waterfalls, all framed by fall’s colors.
The vintage train cars and warm staff only add to the charm of the experience, making it an ideal way to unwind and enjoy the season’s beauty.
Must-see highlight: The Notch Train’s traverse across the Frankenstein Trestle, a historic railway bridge that provides sweeping views of the surrounding mountains and forests.
Best Time to Go: Late September to mid-October, when fall foliage is at its peak and the weather is crisp and clear.
Conclusion
There is no season in New England like autumn, with all its beauty, traditions, and memorable experiences.
Whether it’s a drive along the fall foliage of the Kancamagus Highway, touring the charming covered bridges of Vermont, or visiting a festival, like the Deerfield Fair, there are endless ways to celebrate the enchantment of autumn.
If you’re a local or a visitor, these five classic experiences belong at the top of your New England autumn bucket list.
So, pack up your bags, take your camera, and make an addition in one of the most beautiful areas of the world.
