5 Scenic Itineraries for a 3 Day New England Fall Road Trip

Planning a 3 day New England fall road trip but worried you don’t have enough time? The truth is, most people can’t take off two weeks to explore every corner of New England.

But the good news is, you don’t need that much time to still experience the fall foliage, charming towns, and classic drives this region is known for!

This guide is all about PTO-friendly options. I’ve put together five different 3 day New England itineraries, each one designed to fit into a long weekend. Some focus on scenic mountain routes, others on small-town charm, and one is even doable without a car if you’d rather skip the rental.

By the end, you’ll have several ideas for a New England weekend getaway that shows off the very best of fall in just a few days.

Disclaimer: Some of the links in this post are affiliate links, which means I may earn a small commission if you make a purchase, at no extra cost to you.

Good to Know Before Your 3 Day New England Fall Road Trip

🍁 When is the best time for a New England fall road trip?

Peak foliage usually happens from late September to mid-October, but it depends on the region. Vermont and New Hampshire turn earlier, while Massachusetts and coastal Maine peak a bit later. Since you only have three days, check the foliage tracker and choose the route that matches your dates.

✈️ Where should you start your trip?

It really depends on which itinerary you choose. Most options work best starting from Boston, since it’s the biggest airport hub with the most flights and car rentals. But if you’re focusing on northern Vermont, flying into Burlington might save time, and for an Acadia-focused weekend, Portland is a better bet.

🚗 Do you need a car for this trip?

For most of these itineraries, yes, especially if you want to drive scenic roads like the Kancamagus Highway or visit small towns like Woodstock. A rental gives you the flexibility to stop whenever you want for photos. I recommend checking Discover Cars for the best deals!

📆 Should you book in advance?

Definitely! Fall weekends in New England are busy, and hotels in popular foliage towns can sell out months ahead. The same goes for timed attractions like Flume Gorge. If you only have a long weekend, it’s best to lock in everything early and choose flexible options in case the foliage shifts.

Option 1: Stowe, Vermont

If you only have a long weekend, Stowe is one of the best picks for a 3 day New England fall road trip. It’s full of mountain views, waterfalls, covered bridges, and a cozy downtown, so you get the classic Vermont experience without covering huge distances.

Stowe is about 3.5 hours from Boston or 45 minutes from Burlington, which has a regional airport and plenty of rental cars. Both are convenient starting points, but Burlington makes it especially easy if you’re flying in.

On your first day, explore Stowe Village, grab coffee at one of the local cafés, and walk the Recreation Path. Later, drive through Smugglers’ Notch, one of the most scenic foliage routes in Vermont, and stop at the Grist Mill Covered Bridge before heading back for dinner.

Day two is perfect for the outdoors. Take the gondola up Mount Mansfield for sweeping views, hike to Bingham Falls or Moss Glen Falls, and finish with drinks or dinner at the Trapp Family Lodge.

For your last day, you can take it easy with a short trip to Waterbury to visit Ben & Jerry’s and Cold Hollow Cider Mill, or head to Burlington. If you’re flying out, it makes a natural last stop, with a fun downtown on Lake Champlain and plenty of breweries and restaurants.

Stowe is a popular fall destination, and hotel options are limited, so it’s best to book early. For ideas, check Topnotch Resort for a luxury stay or Green Mountain Inn for a central location.

If you’d like to plan out every stop and need more details, check out my complete 3-day Stowe itinerary for more info!

Option 2: Woodstock, Vermont & Kancamagus Highway

This 3 day New England road trip combines the best of two states, Vermont and New Hampshire. It’s a bit fast-paced, but in exchange, you can visit some of the most stunning fall spots in New England in just a weekend!

Start your trip in Woodstock, one of the most beautiful small towns in New England, especially in the fall.

On your first day, spend time walking through the village, visiting the Middle Covered Bridge, and exploring Billings Farm and Museum. The town itself is very walkable, with plenty of cute shops and cafes to enjoy along the way.

On day two, head just outside town to visit Sugarbush Farm, known for its maple syrup and cheeses, then stop at the Taftsville Covered Bridge before making your way to Quechee Gorge.

From there, drive over to Lincoln, New Hampshire, where you can choose between visiting Flume Gorge, hiking up to Artist Bluff, or even doing both if you have enough time before dinner.

Day three is all about the Kancamagus Highway. It’s one of the most famous drives in New England, especially in the fall, and it gets very busy on weekends. Plan for an early start to enjoy the scenic overlooks, short hikes, and covered bridges without the worst of the crowds.

If you still have some time afterward, you can continue toward North Conway for a walk through town or head up into Crawford Notch before making your way back to Boston.

For accommodation, it works best to book one night in Woodstock and another one or two nights in Lincoln. In Woodstock, 506 On The River Inn is a cozy riverside option, while Woodstock Inn & Resort puts you right in the middle of town.

In Lincoln, RiverWalk Resort at Loon Mountain has large rooms with mountain views, and Holiday Inn Express & Suites Lincoln East is a good choice if you’re looking for something simpler.

If you want to dive deeper into the area, check out my weekend in Woodstock guide and my detailed guide to the Kancamagus Highway.

Option 3: White Mountains & Dixville Notch

If you’d rather skip Woodstock and just focus on the White Mountains, this route is a great pick for a New England weekend getaway.

You’ll still get the classic New England fall colors along the Kancamagus Highway, plus you can add a full day trip to Dixville Notch, which is one of the most striking foliage spots in New Hampshire.

Spend your first afternoon in Lincoln, which makes a handy base. You can walk through Flume Gorge or hike up to Artist Bluff for sweeping views of Echo Lake. Both are really scenic options and if you have the time, I recommend doing both!

Day two is dedicated to Dixville Notch. It’s about 1.5 hours north of Lincoln, so set aside the whole day. The Table Rock hike is the big draw, with its cliffside views over the valley, but you’ll also want to stop at Lake Gloriette and maybe visit a few waterfalls in the area.

It feels much less visited than the southern White Mountains, so it’s worth the drive if you’re planning a mini New England fall road trip.

On your last morning, plan to drive the Kancamagus Highway. The road runs for 34 miles between Lincoln and Conway, with plenty of overlooks, covered bridges, and trailheads along the way. Sabbaday Falls is one of the best stops, so don’t miss that!

It can get really busy on fall weekends, so it’s best to start early if you want to enjoy the drive without the crowds. If you still have time before heading back to Boston, you could continue on to Mount Washington, Crawford Notch, or North Conway.

For hotels, Lincoln doesn’t have a huge number of options, so booking early is smart. Please refer back to Option 2 for hotel recommendations!

For more inspiration, check out my full guides to the White Mountains in the fall and Dixville Notch.

Option 4: Portland & Acadia National Park

If you’re after ocean views, lighthouses, and dramatic coastal scenery, this is one of the best options for a 3 day New England fall road trip.

It works best if you fly in and out of Portland, since trying to squeeze Boston to Acadia into a weekend isn’t really doable. I do have a full 7-day Boston to Acadia itinerary if you have more time!

Start your weekend in Portland. Wander the Old Port District, grab a Holy Donut, and check out Portland Head Light in Cape Elizabeth. It’s an easy-going city that’s super walkable, and there’s no shortage of cozy restaurants and craft breweries for a laid-back first evening.

On day 2, head north to Acadia. You can take the faster inland route if you want to spend more time in the park, or stick to the coast for a more scenic drive. Camden makes a great stop if you choose the latter. Mount Battie has incredible views over the harbor and fall foliage!

Once you arrive in Bar Harbor, explore the town, grab dinner, and drive up Cadillac Mountain for sunset. Just note that you’ll need to book a vehicle reservation in advance for Cadillac!

Spend your final day enjoying Acadia National Park. Drive the Park Loop Road, check out Thunder Hole, walk along Sand Beach and Otter Cliffs, and squeeze in a short hike like the Beehive Trail if you’re feeling active.

For where to stay, I recommend booking one night in Portland and one or two in Bar Harbor, depending on your return flight.

In Bar Harbor, check out Bar Harbor Grand Hotel or Acadia Hotel Downtown. In Portland, The Press Hotel or Hampton Inn Portland are both great picks.

For more details, you can also check out my full guides to one day in Portland and one day in Acadia National Park.

Option 5: Boston and Salem

If you want to enjoy a New England fall getaway without renting a car, this Boston and Salem combo is a great option. It’s not a traditional 3 day New England fall road trip, but it’s perfect for a PTO-friendly weekend with easy public transportation.

Start your trip in Boston, where you can spend the day walking the Freedom Trail, exploring Beacon Hill, and relaxing in Boston Common. Grab lunch in the North End and maybe take a duck boat tour or check out a rooftop bar in the evening.

On day two, take the commuter rail from Boston’s North Station to Salem. The ride takes about 30 minutes, and trains run frequently.

Salem is one of the most popular fall destinations in New England, especially around Halloween. Visit the Salem Witch Museum, explore the historic downtown, and take a haunted walking tour or pop into the Witch House. If you go in October, expect big crowds – but it’s part of the fun!

For day three, your plans depend on your flight. If you’re flying out of Boston in the afternoon or evening, use the morning to explore more of the city. You could visit the Isabella Stewart Gardner Museum, stroll through the Seaport, or grab brunch in the South End before heading to the airport.

But if you have the whole day free and want to experience some foliage, consider booking a guided day tour to the White Mountains. It’s a long day, but it gives you the chance to see peak foliage in one of the most scenic parts of New England, no rental car required.

For hotels, try staying near Back Bay or the Boston Common area for easy access to both city sights and public transit. The Godfrey Hotel and Harborside Inn are both solid picks with great locations and good fall rates if you book early.

Want more ideas? Check out my best things to do in Boston for first-timers, and my one day in Salem itinerary for tips on what to do, where to eat, and how to make the most of your time.

If you’re planning more time in Boston, check out my guide about the best things to do in Boston, how to spend a weekend in Boston, and my one day in Salem itinerary for more ideas!