A fall weekend in New England gives you the best mix of crisp air, colorful foliage, and classic apple orchards. Starting in Hartford, Connecticut, you can head north into the rolling hills and mountain roads that show off the season at its peak. This itinerary takes you from apple picking in family-run orchards to scenic drives through the White Mountains and quiet Vermont towns, all in just two days.
You’ll taste fresh cider donuts, fill a bag with apples straight from the tree, and stop at farm stands that line the backroads. The drive itself becomes part of the adventure, with winding routes that open up to sweeping views of red, orange, and gold leaves. Along the way, you’ll find small towns that invite you to slow down, walk their main streets, and enjoy local flavors.
By the time you reach Vermont, the pace shifts to covered bridges, maple stands, and more orchards tucked into valleys between mountains. This weekend plan gives you a clear route to follow and plenty of ways to enjoy the best of fall without rushing.
Planning Your New England Fall Weekend
You’ll want to time your trip right, pack smart for crisp days and chilly nights, and plan for easy driving between orchards and foliage routes. A little preparation makes your weekend smoother and lets you enjoy the best parts of a New England fall.
Best Time for Peak Foliage and Apple Harvest
Foliage in New England usually peaks from late September through mid-October. The northern states like Vermont and New Hampshire reach color first, while southern areas like Connecticut and Rhode Island peak later in October. Checking a New England peak foliage map before your trip helps you match your drive with the brightest colors.
Apple season overlaps perfectly with foliage season. Orchards in Vermont, New Hampshire, and western Massachusetts typically open for picking from mid-September through mid-October. This means you can plan an apple-picking stop alongside your fall foliage itinerary without missing either highlight.
If you only have a weekend, aim for early October in northern New England or mid-October further south. That timing gives you the best chance to see both vibrant leaves and full baskets of apples.
What to Pack for Sweater Weather Adventures
Days can be sunny and mild, but mornings and evenings often drop into the 40s. Dressing in layers is key. Start with a t-shirt or long sleeve, add a flannel or sweater, and keep a light jacket handy. A warm hat and gloves come in handy for chilly orchard mornings.
Footwear matters too. Many orchards and trails get muddy, so bring sturdy boots or sneakers you don’t mind getting dirty. Pack extra socks in case you step into damp grass or puddles.
Don’t forget a small backpack for snacks, water, and any apples you pick. A thermos of hot cider makes for a cozy break between drives.
Getting Around: Car Rentals and Scenic Drives
You’ll need a car to reach orchards and mountain roads. If you’re flying in, book a rental early since fall weekends are busy. Choose something with good trunk space for apple bags and farm stand finds.
Scenic drives are part of the fun. The Kancamagus Highway in New Hampshire, Vermont’s Route 100, and the Berkshires in Massachusetts are classic leaf-peeping roads. Each offers overlooks, covered bridges, and small towns worth a stop.
Plan your route with extra time for detours. A short side road often leads to quiet views, hidden orchards, or a local farm stand. That flexibility makes your New England fall foliage itinerary feel less rushed and more memorable.
Day 1: From Hartford to the White Mountains
You’ll start your trip in Connecticut and head north into New Hampshire. Along the way you’ll stop for apple picking at one of the region’s oldest orchards before continuing into the White Mountains, where a small town base gives you easy access to foliage views, cider donuts, and local dining.
Start in Hartford: Coffee and Road Trip Prep
Begin your morning in Hartford with a quick breakfast and coffee before hitting the road. A local café like Story and Soil Coffee makes a good stop if you want something quick but high quality. Grab a pastry or sandwich to keep you full for the first leg of the drive.
The trip from Hartford to the White Mountains takes about 3.5 to 4 hours without long stops. Leaving early helps you avoid traffic and gives you more time to explore later in the day. Pack some snacks and water so you don’t need to stop too often along the highway.
If you’re traveling with kids, make sure to bring along games, books, or music. The drive is scenic once you get into New Hampshire, but the first stretch is mostly highway. A little planning makes the morning smoother and keeps everyone in good spirits.
Applecrest Farm Orchards: Classic Apple Picking
Your first big stop is Applecrest Farm Orchards in Hampton Falls, New Hampshire. This orchard is about halfway between Hartford and the White Mountains, making it a perfect place to stretch your legs. It’s one of the oldest continuously operated orchards in the country, and it offers a wide variety of apples in the fall.
You can pick your own apples, explore the farm store, and grab seasonal treats. Families especially enjoy the wagon rides and kid-friendly activities on weekends. The orchard also has a market with fresh pies, cider, and produce if you want to stock up for the rest of your trip.
Plan to spend about an hour here. It’s enough time to pick a bag of apples, walk the rows of trees, and enjoy the farm atmosphere before getting back on the road toward the mountains.
Exploring North Conway: Small Town Charm and Cider Donuts
By late afternoon, you’ll arrive in North Conway, a small town in the White Mountains that makes a great base for the weekend. The downtown area has shops, cafés, and plenty of spots to walk around after a long drive.
Make sure to stop at White Mountain Cider Co. in nearby Bartlett for fresh cider donuts. They’re made daily and are a fall favorite. You can grab a box to enjoy right away or save them for breakfast the next morning.
For dinner, try the Muddy Moose Restaurant in North Conway. It’s casual, kid-friendly, and serves hearty meals that hit the spot after a day of driving. If you have extra energy, take a short walk through town before heading to your hotel or inn for the night.
White Mountains Foliage Adventure
You’ll find some of the best fall scenery in New Hampshire inside the White Mountain National Forest. A drive here mixes winding roads, short hikes, and classic covered bridges that capture the charm of a New England autumn.
Kancamagus Highway: Scenic Byway and Covered Bridges
The Kancamagus Scenic Byway runs 34 miles between North Conway and Lincoln. Locals call it “the Kanc,” and it’s one of the most popular drives for leaf peeping. The road climbs through mountain passes, following the Swift River, with frequent pull-offs for photos.
You’ll spot brilliant reds and oranges in early to mid-October, which is usually peak foliage season. If you’re flexible, check the New Hampshire foliage tracker before your trip to time it right.
Along the way, you’ll find small parking areas near scenic overlooks. Popular stops include Sugar Hill Scenic Vista and Pemigewasset Overlook. Both give you wide views of the valleys and ridges.
Don’t rush this drive. Even though it takes less than an hour without stops, you’ll want at least half a day to enjoy the views, walk around, and snap photos.
Sabbaday Falls and Rocky Gorge: Short Hikes and Photo Stops
Sabbaday Falls is one of the easiest waterfall hikes in the White Mountains. The trail is less than a mile round trip, with a gentle incline that makes it doable for almost anyone. At the end, the falls drop into a narrow gorge with wooden railings and bridges that give you safe viewpoints.
Not far down the road, you’ll reach the Rocky Gorge Scenic Area. This spot has a short path that leads to a rushing gorge carved by the Swift River. The water flows through smooth rock channels, and the surrounding trees light up with color in October.
Both stops are quick but worth it. You can park, stretch your legs, and take in the scenery without committing to a long hike. These are also great places for photos if you want a mix of water and foliage in the background.
Albany Covered Bridge: Iconic Leaf Peeping Spot
The Albany Covered Bridge sits just off the Kancamagus Highway near Conway. Built in the 1850s, it crosses the Swift River and remains one of the most photographed bridges in New Hampshire. In fall, the red bridge framed by golden maples makes a classic New England scene.
You can drive across the bridge or park nearby to walk around. The riverbanks offer nice angles for photos, especially in the late afternoon when the sun hits the trees.
If you want to explore more, there are short trails leading from the parking area into the White Mountain National Forest. Even a short stroll gives you a quieter view of the leaves away from the main road.
This is a simple stop, but it captures the charm of the region and pairs perfectly with the longer drives and hikes nearby.
Day 2: Vermont’s Quintessential Fall Experience
You’ll spend the day surrounded by colorful foliage, crisp mountain air, and some of Vermont’s most classic fall traditions. From apple picking to cider tasting and a family-friendly corn maze, each stop gives you a true taste of the season.
Stowe: Burtt’s Apple Orchard and Maple Creemees
Start your morning in Stowe at Burtt’s Apple Orchard, a spot known for its wide variety of apples and beautiful mountain views. The orchard is easy to explore, and you can pick your own apples straight from the trees. Rows are clearly marked, so you know exactly which varieties are ready.
After filling your bag, treat yourself to a maple creemee, Vermont’s signature soft-serve ice cream. Burtt’s makes theirs with local maple syrup, giving it a smooth, rich flavor that’s different from anything you’ll find outside the state.
Take a short walk through the orchard before leaving. The views of the surrounding hills, especially if you check the Vermont foliage report ahead of time, can be some of the best of the season.
Cold Hollow Cider Mill: Cider Donuts and Hard Cider
Next, head to Cold Hollow Cider Mill in Waterbury. It’s one of the most popular stops in the area for good reason. The smell of fresh apple cider donuts hits you as soon as you walk in, and you can watch them being made on the old-fashioned machine.
The store also sells fresh-pressed cider, maple products, and local snacks. If you want something a little stronger, stop by the tasting room for a hard cider flight. The ciders range from crisp and dry to lightly sweet, so it’s easy to find one you like.
Grab a cup of hot mulled cider to-go before you leave. It’s the perfect drink for your next scenic drive through the Green Mountains.
Percy Farm Corn Maze: Fall Fun for All Ages
End the afternoon at Percy Farm Corn Maze in Stowe. The maze is set against a backdrop of rolling hills and bright foliage, making it a fun and seasonal way to enjoy the outdoors. Paths are well-kept, and the layout changes each year, so it feels fresh even if you’ve visited before.
Families can take their time exploring, while kids love the challenge of finding the exit. If you’re not in a rush, wander the farm stand for pumpkins, gourds, or other fall produce.
It’s a relaxed way to wrap up the day, and the views of the mountains glowing with fall color make it especially memorable.
Classic Vermont Foliage and Small Towns
You’ll find some of the best foliage in Vermont by pairing winding mountain drives with quiet towns and historic spots. The mix of scenic passes, alpine-style lodges, and postcard farms gives you a full range of what makes this part of New England so memorable in the fall.
Smugglers Notch: Dramatic Passes and Leaf Views
Driving through Smugglers Notch feels like slipping into a hidden corner of the Green Mountains. The narrow road twists between tall cliffs, with sharp turns that keep you slowing down to take it all in.
During peak foliage, the trees crowd the road in shades of orange, red, and gold. There are small pull-offs where you can stop, stretch, and snap photos of waterfalls or mossy boulders.
This route is short, but it’s packed with views. A compact car makes the drive easier since larger vehicles can feel tight in the bends. Plan on taking your time here, because even though it’s only a few miles long, you’ll want to stop more than once.
Von Trapp Family Lodge: Alpine Vibes and History
Just outside Stowe, you can visit the Von Trapp Family Lodge, built by the family made famous in The Sound of Music. They chose this hillside location because it reminded them of Austria, and you can see why once you look out at the rolling mountains.
The lodge grounds have trails, meadows, and wide views that feel peaceful in the fall. Even if you don’t stay overnight, you can walk the property or enjoy a drink at the café.
If you do book a room, the Woodstock Inn & Resort is another great option nearby, but the Von Trapp Lodge stands out for its alpine character and family history. It’s a good place to pause, relax, and enjoy the slower side of the trip.
Woodstock: Sleepy Hollow Farm and Artist Bluff
The town of Woodstock is one of Vermont’s most photographed small towns. White steeples, covered bridges, and tidy shops give it a classic New England look. In autumn, the hills around town glow with color.
A short drive from the center brings you to Sleepy Hollow Farm, a private property often photographed from the roadside. The view of the farmhouse framed by maples makes it one of the most iconic fall scenes in Vermont.
For a different perspective, head toward Artist Bluff. The short hike gives you a wide overlook of rolling hills and foliage that stretch for miles. Between the farm views and the bluff, you’ll see both the quiet charm of the countryside and the scale of Vermont’s fall colors.
Wrapping Up: Scenic Routes and Local Flavors
As the weekend winds down, you can still enjoy a few more drives and stops that highlight the best of New England. Scenic roads, small-town markets, and simple choices on the road will help you end your trip on a relaxed note.
Route 100 and The Berkshires: Final Leaf Peeping Drive
If you’re heading south from Vermont, Route 100 makes a perfect last stretch. This road runs through the Green Mountains and gives you constant views of rolling hills, covered bridges, and small farm towns. It’s one of the most photographed routes in New England during foliage season.
Driving further west, you can cut across into The Berkshires in western Massachusetts. The area is dotted with art museums, historic villages, and winding backroads lined with maples. Towns like Stockbridge and Lenox offer easy places to stop for coffee or a quick bite.
This route works well if you’re returning home toward New York or Connecticut. It keeps you off the highways and gives you a slower pace to enjoy the last of the leaves before you wrap up your weekend trip.
Farm Stands and Pumpkin Patches: Last-Minute Stops
Along backroads in Vermont, New Hampshire, and Massachusetts, you’ll see plenty of farm stands. Many are simple roadside tables with baskets of apples, jars of maple syrup, or fresh cider. These are great places to grab snacks for the drive home.
If you still want that classic fall photo, stop at a pumpkin patch. Orchards often pair apple picking with pumpkins, so you can pick one up without going out of your way. It’s an easy way to bring a bit of the season back with you.
Some orchards also sell cider donuts, jams, or local cheeses. Packing a small cooler in your car helps you take these treats home without worrying about them spoiling on the road.
Tips for Sustainable Fall Road Tripping
Keeping your trip low-impact makes a difference, especially in small towns that see heavy fall traffic. Start by bringing a reusable water bottle and coffee mug so you don’t collect extra cups along the way.
When you shop at farm stands or orchards, carry a tote bag instead of using plastic. Many places even offer discounts if you bring your own.
Driving early or late in the day helps you avoid traffic jams, which saves fuel and cuts down on idling. If you’re renting a car, choose a smaller or hybrid model since narrow mountain roads are easier to handle in compact vehicles.
Supporting local orchards, markets, and family-run diners also keeps your dollars in the community you’re visiting. That way, your fall road trip itinerary not only gives you memories but also helps sustain the places you enjoyed.
