New England Fall Road Trip: 7 Days in Vermont & New Hampshire

After relocating back to the U.S. a few years back and settling into our new home base in Connecticut, we planned a number of long weekend trips to visit different parts of New England. Some of my favorites included a visit to Vermont’s most charming towns in winter, a long weekend exploring the Berkshires in Massachusetts, and a family-friendly getaway to Upstate New York’s sprawling countryside and eclectic small towns.

Each trip made me more convinced I needed to plan out the perfect New England fall road trip itinerary when the leaves were changing colors. Road trips are one of my favorite ways to travel, and I wanted to dedicate a week to exploring the most iconic parts of New England during the fall season. However, in planning this trip I was working with two new elements: bringing along a baby, and necessary logistics of having to plan the trip months in advance (despite wanting to be flexible to take off during ‘peak’ leaf peeping week!).

Here’s how I went about planning this fall-inspired drive, what some of our favorite highlights were, and what I’d do differently the next time around.

About This Road Trip

This itinerary moves from New Hampshire to Vermont, spending four nights in the White Mountains (a sprawling region of New Hampshire with some of the most jaw-dropping fall colors on the east coast) before driving west into Vermont’s hill country for the second half.

In researching the most iconic spots for this trip, it quickly became clear to me that many of the photos I associated with a ‘New England Fall Trip’ were taken in and around New Hampshire’s Kancamagus Highway. For that reason, I knew multiple nights in New Hampshire was a must; both for ease of exploration and the ability to adapt based on weather as needed.

The second portion of the trip, Vermont, was focused more on effortlessly photogenic scenes: historic towns and villages, charming inns and B&Bs, scenic drives and quaint shops. This portion of the trip was a bit more relaxed and accessible, perfect for wandering and decompressing after seeking out dramatic New England landscapes.

The Big Booking Question: Plan Ahead or Book Last Minute?

What makes planning a New England fall road trip a bit tricky is that peak foliage doesn’t happen on the same dates every year. In New Hampshire, the northern White Mountains and higher elevations typically peak late September to early October. Vermont’s lower valleys, for example, Woodstock, Pomfret, and Route 100, tend to peak a week or two later. So using the word “typical” is loose; timing can shift by a week or more depending on the season. That leaves two options for planning this type of road trip:

Option 1: Book in advance, accept the trade-off. Better properties, better prices, and no scramble to book, but you’re locking dates without knowing exactly when peak hits. This is the right approach if you have a fixed window, are coordinating with others, or want a specific property (for instance, the popular Woodstock Inn in Vermont and the Omni in New Hampshire book out by August for fall dates in October).

Option 2: Book last minute, adapting based on peak color. Watch the New England fall foliage map and book once peak is visible heading your way. This gives you better odds of catching it at its best, but leaves you incredibly limited with accommodation options. This is certainly tougher if you’re planning around work scheduling or weekend dates. Availability in Woodstock, Stowe, and North Conway is genuinely tight during peak, and you’ll pay more for less.

Given that we were doing this the first time and traveling with our son, we opted to book in advance from peak dates in the seasons before. This felt like the right call for us in terms of comfort and ease of travel. It did mean that we experienced dramatically beautiful fall colors in New Hampshire (as was my priority), and less peak oranges and reds in Vermont.

Hotel Tip: Book the Omni and the Woodstock Inn at least 3-4 months out for October dates. Both hotels are in high demand during foliage season.

Trip Highlights

Polly’s Pancake Parlor in Sugar Hill, NH – legendary breakfast spot since 1938, buckwheat/whole wheat/oat-buttermilk pancakes with real maple syrup, hilltop dining room overlooking the White Mountains. This was a fun morning outing, though I wouldn’t visit just for the pancakes alone – the full experience is the real draw. 

Cloudland Road in Pomfret, VT – A dirt road lined with fall color, rolling hills, and quiet farms. The farm opposite Elm Grove Farm on Google Maps (known as Sleepy Hollow Farm) is the most famous photo stop in the region, but worth noting it wasn’t accessible to us during our visit as the road gets blocked off now during peak fall season from crowds.

Maple Creemees at Woodstock Scoops, VT – I’m addicted to the taste of this delicious soft serve ice cream infused with local maple syrup, a true Vermont treat! Best enjoyed in combination with a scenic walk through downtown. 

Sugarbush Farm in VT – this was a great afternoon stop to see how maple syrup is collected, taste different varieties, and take home some of our own jugs. It’s a charming farm as well to wander and explore the grounds. 

Rocky Gorge on Kancamagus Highway, NH – this stop along this scenic drive, famous for its red and orange landscapes, was breathtaking. Between the river scenery, the colors, and the short walk to see Falls Pond (and surprisingly, have it to ourselves!), we definitely found this to be a worthwhile stop.

White Mountain Cider Co., NH – a charming little roadside stop for food and snacks off the Kancamagus Highway. Don’t forget to grab their freshly made apple cider.

Visiting the Simon Pearce Studio in Quechee, VT – A glass and pottery studio in a converted mill on the Ottauquechee River, with a restaurant and shop. My son loved watching the live demonstration of how they blow glass, and we took home a couple of beautiful vases that are on constant display in our home now. 

Apple Picking at Green Mountain Orchard in Putney, VT – a picturesque spot for pick-your-own apples and other fruits. 

Shopping at Farmhouse Pottery in Woodstock, VT – I’ve always been a fan of this homeware brand, so visiting their flagship store was a must. 

Where to Stay

To keep our schedule as simple as possible, we narrowed down our bases to only two locations: a hotel in the White Mountains, NH, and an Airbnb in Woodstock, VT, both of which are anchored 30-45 minutes from the day’s main stops. That meant we could keep the driving to a minimum, and base ourselves in the best parts of the east coast for colors. The only exception to this driving distance is Kancamagus Highway: plan for at least 2.5-3 hours to do the full driving loop and make some stops along the way.

New Hampshire Base: Omni Mount Washington

In researching where to stay near the main leaf peeping sights in New Hampshire, the Omni Mount Washington showed up constantly. At first I’d planned to stay somewhere smaller, opting for a B&B or boutique hotel, but I wasn’t particularly inspired by the inventory and everything that jumped out at me ended up being less convenient to the spots I wanted to see. 

Eventually I decided to just go for it and book the Omni; it was an experience in itself, with a bustling scene, cushy couches in front of fireplaces, and rooms that felt a bit like stepping back in time.

Hotel Tip: The Omni is a splurge property, but we got lucky on pricing for our dates. If you’re flexible during the week or don’t mind hedging your bets on timing, you can often find a more affordable room.

For the sake of simplicity, it ended up being perfect for our needs, and traveling with a baby meant we could actually enjoy dinner down the hall at the restaurant when our son went to bed. Bonus! 

The Omni Mount Washington and the Omni Bretton Arms (their adjacent inn, a walk away) sit on the same grounds in Bretton Woods, at the base of Mount Washington. It’s a National Historic Landmark with views of the Presidential Range that are spectacular in fall.

Additional Hotels & Airbnbs in New Hampshire

As much as I enjoyed the Omni for our first visit, I wouldn’t be in a rush to book it again given its high price point. For a next visit, I have my eye on two other properties near this region: Under Canvas White Mountains, a luxury glamping property with a restaurant that immerses you in nature, and Rabbit Hill Inn, a charming historic New England hotel on the Connecticut River (this property is actually located on the Vermont side, just over the border of New Hampshire, but still accessible to New Hampshire’s fall stops).

RiverWalk Resort at Loon Mountain – $$ – a popular spot to stay in the nearby town of Lincoln, with mountain views and easy access to the Kancamagus Highway. 

Under Canvas White Mountains – $$$ – the ultimate luxury glamping retreat with a restaurant, located in nature just above some of New Hampshire’s best fall sights. 

Rabbit Hill Inn – $$$ – a historic, charming B&B that’s worth booking in advance to experience true New England hospitality. 

Airbnbs are ideal if you’re after your own space. I’d look at Lincoln for easy access to the Kancamagus Highway and nearby North Conway for more of a small town village vibe. 

– This tiny timber home in Lincoln offers a unique stay with a fire pit and barbecue. 

– My top picks in North Conway include this modern A-frame cabin and this cabin on an acre of land with a great game room. 

– This charming cottage on the water also caught my eye for a return visit. 

Vermont Base: The Woodstock Inn & Resort

Vermont is magical. Every time I visit I find something new to love here – beyond the quaint towns (Woodstock is one of my all-time favorite US towns), the maple creemees (a must-try local treat: soft serve ice cream made with Vermont maple syrup), and the low-key style of shops and restaurants, it’s a beautiful state with plenty to explore. 

While we would’ve loved to stay at The Woodstock Inn & Resort, and it remains my top recommendation for this portion of the trip, we made a last-minute call to switch to an Airbnb rental (sadly, no longer listed but I list similar ones below) so we could have a kitchen with a baby. I really enjoyed having a true ‘home’ base here, but that said, it was a bit removed from town.

I would absolutely spring for a room at Woodstock Inn if I were planning this trip again. There’s a reason it tops New England hotel lists, and the location in the center of town can’t be beat. 

The town of Woodstock, Vermont, feels like stepping into a movie set. Between the iconic village green, covered bridges, stone storefronts and quaint antique shops, it’s a charming place to visit and base yourself in. Staying in the center at Woodstock Inn puts you near Pomfret and Cloudland Road to the north, and Quechee just 15 minutes east.

Additional Hotels & Airbnbs in Vermont

In addition to the iconic Woodstock Inn & Resort, my top pick for where to stay, here are some other properties I’d consider booking, especially in nearby Pomfret and Hartford: 

The Woodstocker B&B – $$ – a cozy, warm 9-room inn located in the heart of Woodstock, within walking distance to plenty of shops and restaurants. Books up early; worth checking The Vesper down the road if it’s full.

The Jackson – $$$ – a boutique inn and restaurant just a short walk from Woodstock’s village green, known for its gardens and elevated on-site dining.

Beyond the above hotels mentioned that are both situated walking distance from the center of Woodstock village, I’d opt for a hotel that’s a short drive into town (my top pick is the Deer Brook Inn, followed by the Kedron Valley Inn), or an Airbnb. Choosing a unique Airbnb property within a short drive is a great alternative, as the hotels often book up by mid-summer.

– This converted luxury barn retreat is my top pick in the area for a charming stay. 

– For a cabin experience, check out the nearby Greydon Cabin or this woodsy A-frame cabin. 

– This unique farm stay oozes with New England charm in nearby Hartland. 

– Nearby Wheelock Hideaway is great for families or groups, as well as this hillside retreat in Pomfret. 

New England Fall Colors Map

To make it easy for you to track the best spots for fall colors and hit all the places mentioned in this guide, I’ve created a New England Fall Colors map below. My hotel recommendations for New Hampshire and Vermont are also featured, as well as my suggestions for additional stays across New England as featured in this post about my favorite boutique hotels.

My 7-Day New England Fall Road Trip Itinerary

Day 1: Drive Up + Arrive in New Hampshire

We drove from our home in Connecticut, but many people opt to fly into nearby Boston Logan airport. Boston to Bretton Woods, New Hampshire, is roughly a 2.5-3 hour drive. 

As we drove up, we were most interested in hitting farms nearby to kick off our trip. The farm stops on my list for this day: Lull Farm, Sunnycrest Farm, Lavoies Farm, and Gould Hill Farm.

Alternatively, if you have time before check-in: Flume Gorge is ~30 minutes from the Omni (even just the entry area and covered bridges are worth a stretch, but save the full loop for later). Blair Covered Bridge (~45 min from the Omni) is a classic NH photo stop.

Check in to the Omni hotel, settle in and have dinner on your first night.

• Drive: ~2.5-3 hrs from Boston
• En route: Farm stand stops
• Optional: Flume Gorge (quick look) or Blair Covered Bridge
• Evening: Check into the Omni, dinner on property

Tip: If you’re short on time, you can also book this highly rated tour of the fall foliage along the Kancamagus Highway by bus, which departs from Boston.

Day 2: Artist’s Bluff

A 1.4-mile round-trip hike from the Echo Lake parking lot to a hilltop overlooking the lake and Franconia Notch. This hike is short with some elevation gain but accessible for most fitness levels.

Alternatively, if the weather isn’t on your side (as was the case for us), there are a number of roadside sights and stops you can hit all nearby the Omni. Silver Cascade Waterfall is an easy one, a scenic waterfall just off the road in the midst of the changing fall leaves. 

In the afternoon, make the half-hour drive to the quaint town of Littleton. Here you can visit the Riverwalk Covered Bridge, do some antiquing, and peruse the wares at White Mountains Canning Company (treat yourself to some homemade ice cream or a milkshake while you’re there).

• Morning: Artist’s Bluff (1.5-2 hrs with time at the top) or nearby roadside stops like Silver Cascade Waterfall
• Afternoon: Littleton (30 min drive)

Day 3: Kancamagus Highway + Flume Gorge

This is your most packed day, visiting the iconic Kancamagus Highway. It’s a 34-mile loop through White Mountain National Forest, and it’s not a drive to rush. Leave mid-morning, driving from the Omni to North Conway before making your way west along the Kancamagus Highway.

Stops we hit on the Kancamagus Highway included the Albany Covered Bridge (an iconic bridge that makes most fall road trip lists), Rocky Gorge (including Swift River, Falls Pond and Lower Falls, so a great 3-in-1), and the Lincoln Woods Trailhead (for a nice short and scenic hike). If I went again, I would also want to stop at Sabbaday Falls. 

Note: Lincoln Woods Trailhead is partially closed June – November 2026 for required repairs. Check the park website for affected areas and updates.

It’s worth noting that if you do this drive during peak season, you may end up stuck in traffic. We were fine for the first ¾ of our drive, and then got stuck bumper to bumper on the last portion and what should’ve been 20-30 minutes took us almost 2 hours. I’d recommend packing some snacks, drinks and entertainment in the car so you’re prepared if this happens to you!

Be sure to stop off in North Conway for lunch at White Mountain Cider Co. during the drive. Foodies will enjoy the award-winning fine-dining restaurant, but a casual menu is also available. They have a market and deli with sandwiches, pastries, and tasty pies made in house.

If you’re feeling energetic, you could also include a full stop at Flume Gorge. The hike itself is a 2-mile loop, 1.5-2 hrs, multiple waterfalls, covered bridges, a genuinely dramatic granite gorge. $18 entry. 

• Mid-morning: Kancamagus Highway 
• Along the way: Albany Covered Bridge, Rocky Gorge, Sabbaday Falls
• Midday: Lunch in North Conway at White Mountain Cider Co.
• Afternoon: Kancamagus Highway additional stops or Flume Gorge
• Evening: Back to the Omni

Day 4: Polly’s Pancake Parlor + Slow Day

Make your way to Polly’s Pancake Parlor, Sugar Hill early if you can (around 7:30am if you want to beat the crowds). This is a fun stop for the vibes alone, but the food is also a tasty way to fuel for the day.

We had a slower afternoon this day, as Jacob opted to golf while I explored the grounds of the Omni. You don’t have to be a guest to visit the grounds, and they really are beautiful and worth seeing.

If you’re staying at the Omni, you can ride the Skyway Gondola for free. The 12-minute ride takes you to Rosebrook Lodge which offers gorgeous views, plus there’s a restaurant and cafe at the top if you’d like to stay a while.

Alternatively, make the short drive to Mount Washington Cog Railway. A roundtrip journey to the top is about 3 hours with an hour spent at the summit. The view can be foggy so this is something you’ll do for the experience with a beautiful view being the bonus. Just note it’s chilly up there, so dress accordingly. The Conway Scenic Railroad also offers shorter train journeys (1 hour) and takes you past beautiful fall colors.

Tip: Both train journeys book up weeks in advance during peak fall colors, so try to get tickets early.

• 7:30am: Polly’s Pancake Parlor (reservations recommended on weekends)
• Afternoon: Ride the Skyway Gondola and explore the Omni grounds or ride the Mount Washington Cog Railway (book early)

Day 5: Drive to Vermont via Cloudland Road

Check out of the Omni and head southwest toward Woodstock (~2 hrs driving). Route through Pomfret and down Cloudland Road (dirt road, rolling farmland, and the Sleepy Hollow Farm photo stop, which is the farm opposite Elm Grove Farm on Google Maps).

Tip: While Sleepy Hollow is the most famous photo stop in the region, the road was blocked off during our visit to avoid crowding during peak season. It’s still worth driving Cloudland Road if you can though, as the fall colors there are beautiful.

Check into The Woodstock Inn and rest a little before heading out to explore Woodstock village.

Woodstock village is a perfectly walkable, quintessentially New England town. The village has lots of small local shops to pop in and out of and a charming covered bridge right in town. The red brick buildings and white houses make a stroll around town feel like you stepped right into a postcard.

One place I knew I wanted to visit in Woodstock is the Farmhouse Pottery flagship store. I’m a big fan of this homeware brand, so an opportunity to visit this shop couldn’t be missed.

Anywhere in town is a good choice for dinner, but Oakes & Evelyn is a local favorite. As a farm-to-table restaurant, quality and seasonal ingredients are the main focus, so expect to pay a little more for a great meal.

• Morning: Check out, drive towards Pomfret
• En route: Cloudland Road / Sleepy Hollow Farm
• Midday: Check into The Woodstock Inn
• Afternoon: Woodstock village + Farmhouse Pottery
• Evening: Dinner at Oakes & Evelyn

Day 6: Sugarbush Farm + Woodstock

Sugarbush Farm is a short drive from town down a dirt road. This maple syrup and cheese producer has been run by the same family for four generations. Tour the sugarhouse here, sample maple products (including maple candy), and taste some of their local cheese. We took home two giant jugs of maple syrup, but there are plenty of smaller treats on offer as well. 

Nearby Abracadabra Coffee Co, a charming local coffee spot, is worth going a bit out of the way for. Delicious lattes and brunch, all served inside a converted camper van. Depending on what time you’re up, you can also hit the farmstand across the way, On The Edge Farmstand. 

The rest of the afternoon is yours to explore more of Woodstock. Visit some of the antique shops, people watch at a cozy cafe, and treat yourself to a maple creemee. These local desserts are a combination of creamy soft serve and maple syrup from the local area whipped together into a velvety-smooth treat.

• Morning: Sugarbush Farm (1-1.5 hrs)
• Morning: Abracadabra Coffee Co.
• Afternoon: Explore downtown Woodstock

Day 7: Simon Pearce + Green Mountain Orchard

As you head out of town on your way home, there are a few more stops worth fitting into your New England fall road trip.

Stop by Simon Pearce in Quechee, 15 minutes away from Woodstock. Located inside a restored 19th-century mill, the shop has a huge glass studio (and does glass-blowing demonstrations downstairs) and a restaurant which overlooks a waterfall. There’s also one more covered bridge to take in crossing the Ottauquechee River.

Heading south from Simon Pearce, you’ll follow the Connecticut River to Green Mountain Orchard in Putney (~1 hour). This orchard has been a staple of the area for over a hundred years and is a great stop for apple picking. If you visit in late September, you can also pick your own pumpkins.

If you’d rather not do the work yourself, they have a farm stand where you can grab a fresh-pressed cider, pick up an apple pie to heat at home, or try a cider donut.

• Morning: Simon Pearce in Quechee
• Afternoon: Apple picking at Green Mountain Orchard
• Evening: Final night at your accommodation or depart for home

What I’d Do Differently

If I were planning this trip again, I’d still focus on New Hampshire and Vermont, assuming I wanted to hit the quintessential New England fall color spots. For a first-time trip, I think it covered a lot of major highlights in this region. 

That said, I wish I had known that Kancamagus Highway in particular would be as crowded as it was, and that some spots I anticipated wouldn’t be accessible (e.g. Sleepy Hollow Farm being so photographed that it’s now blocked off).

Ideally, to balance out the more high-traffic areas, I would’ve incorporated a few days in other New England destinations at the start or end of this trip: The Berkshires in Massachusetts, upstate New York in and around Hudson Valley, and charming towns in Connecticut are all good add-on options. Here are some of my favorite stays in and around these areas.

It’s also worth noting that while we enjoyed beautiful fall colors in New Hampshire, when we arrived in Vermont, many leaves had already fallen. So timing this trip to maximize fall colors in both destinations is nearly impossible, as they both have different peak times.

Regardless, we still enjoyed Vermont in fall and this portion of the trip was about maximizing cozy fall vibes, not seeing dramatic landscapes (as was the priority in New Hampshire). 

Practical Tips

Getting There: Boston Logan (BOS) is the closest major airport to fly into. Boston to Bretton Woods, New Hampshire, takes about ~2.5 hrs by car and Boston to Woodstock, Vermont, is about ~3.5 hrs.

Getting Around: Renting a car is essential. Destinations like the Kancamagus Highway, Cloudland Road, Flume Gorge, and Sugarbush Farm aren’t accessible without one.

EV Charging: Lull Farm, Sunnycrest Farm, and Lavoies Farm all have Electrify America charging nearby on the way up. Be sure to plan one charge stop before the White Mountains as infrastructure there is more limited.

Tracking Peak Foliage: The New England fall foliage map is updated weekly starting late summer. Start watching in mid-September if your dates have any flexibility.

Weather: Layers + waterproof jacket are the key. Expect temperatures in the 40s in the morning and mid-60s on a good afternoon. Rain is likely at least once over a week so bring warm, dry footwear.

Parking: Kancamagus Highway pull-outs (Lower Falls, Rocky Gorge especially) fill by mid-morning on weekends, so you’ll want to be early. Flume Gorge’s parking lot fills up too so aim to arrive at opening.

Final Thoughts

This itinerary gives a balance of dramatic landscapes in New Hampshire and cozy villages with slow mornings in Vermont, but if there’s one takeaway from this trip, it’s that you can’t perfectly time the leaves. We booked well in advance based on past peak dates and still caught New Hampshire at its best while Vermont had already dropped a lot of its color. For us, it was a trade-off worth accepting, and if we had it to do over, we wouldn’t change much at all.

FAQs

When is the best time for a New Hampshire and Vermont fall road trip? 

Late September through mid-October, but timing varies by year. The White Mountains and higher Vermont elevations tend to peak late September; Woodstock and the lower Vermont valleys peak early-to-mid October. The first week of October is a reasonable target for catching both close to peak but watch the live foliage map beforehand.

Should I book in advance or stay flexible for New England fall? 

Both options work depending on your priorities. Booking ahead means better properties and prices but fixed dates; booking last minute means being more flexible to visit during peak color but there are far fewer accommodation options.

How many days do you need for a New Hampshire and Vermont fall road trip? 

Seven days covers both states without rushing. Five days works if you trim stops and minimize driving. Ten days is ideal if you want more time in Vermont (Stowe, the Northeast Kingdom) or would like to add Massachusetts, Connecticut, New York, or other areas. 

Is the Kancamagus Highway worth the drive? 

Yes. Covering 34 miles, it features multiple waterfalls and covered bridges. Treat it as a full day and not a drive-through. We drove from east to west to prioritize North Conway and the first few stops, but you could also start east from Lincoln in the morning.

What’s the best base for a New Hampshire fall foliage trip? 

Bretton Woods (Omni Hotel) for the Presidential Range, Crawford Notch, and the Kancamagus Highway. Lincoln is a more affordable alternative at the base of the White Mountains and North Conway has the most restaurants and lodging options.