Fall Leaf Peeping Road Trip Ideas to Help You Hit the Road!

fall foliage

Starting in September, most of the northern parts of the U.S. start to transform from simply pretty to breathtakingly beautiful as trees burst into various shades of red, orange, yellow, and gold. One of my favorite fall road trip ideas is to "follow the wave" of color through New England, from Maine to Massachusetts.

Why New England when the beauty is almost everywhere? Mostly, it’s the remarkable amount of charming towns, pretty churches, and hilly landscapes that lend themselves perfectly to leaf-peeping. If you’ve just seen the fall colors on a flat landscape (like parts of the Midwest), you’ll be overwhelmed when you first view them on a mountainside or hillside. You get these fantastic sweeps of color and gorgeous patchworks of multiple colors on one hillside, views you just can’t get in the plains.

This is one of my favorite road trip ideas because not only have I traveled through all of these states at different times on leaf peeping road trips, I’ve always planned on doing the grand sweep when I had enough time off to really go for it (we’re talking two months here). With only a week or two of vacation, it’s impossible to do this, so either you’ve got the time or you don’t. If you don’t, you could still take this road trip in parts/by state, or check out the other fall leaf peeping ideas and itineraries at the bottom of this page.

To help those of you who only have time for one state, each is presented separately for your convenience. Be aware that the dates of peak fall color vary from year to year – best times/peak color can’t be guaranteed. The dates listed are typical, though.

These road trip ideas were designed to be taken in order, so you could visit each location on this hit-list as you travel.

“Follow the Wave” Road Trip Ideas – New England Leaf-Peeping Extravaganza!

Maine Road Trip Ideas
Best time: 2nd week of September through the end of September/early October

  • Moosehead Lake, Greenville, Maine – This is a wonderful place to visit in the fall as the leaves change. There are tons of outdoor activities including moose safaris (hence the name of the lake), canoeing, day cruises, and a visit to the striking Mt. Kineo (if you’re a hiker, a must-do is to climb it and enjoy the amazing views from the top). What makes viewing fall foliage around a lake special is the reflections of the colors on the water, much like an impressionist painting. One of my favorite fall memories is of canoeing on a lake in the fall in Vermont – wow! You could spend three days here enjoying all the natural beauty, or stick to one or two before moving on.
  • Old Canada Road Scenic Byway – Ride US Route 201 from the hamlet of Jackman to Skowhegan for a leaf-peeping showstopper of a ride. Rivers wind along the side of the road sparkling in the brilliant fall sunlight while mountain ridges decorated with fall foliage rise all around you as you travel. There are many small rustic towns to view as you travel, or you can stop to explore. The entire ride is about two and half hours long – a great way to while away a morning or afternoon.
  • Bangor – Not only is this cultured city home to the famous and beloved huge Paul Bunyon statue as well as horror-novelist Stephen King, it also has many great museums (especially the Forest and Logging Museum and the Maine Discovery Museum), shopping and dining, and plenty of charm. One to two days here will allow you time to take everything in.
  • Acadia National Park – This is a great park to hike or drive through for leaf peeping (it’s a gorgeous park year-round), but also for the many beautiful views of the Atlantic Ocean. No matter what time of year you visit Maine, this park is so special, it’s a must-see. One full day is a must at Acadia – it’s a huge park and you’ll miss so much if you don’t give it enough time. Plan to get out of your car a least a little and explore on foot. Whales can be sighted right from the shores of this park, so you’ll get the chance to do some whale watching without having to pay a penny for a tour (though there are many wonderful tours out of nearby Bar Harbor).
  • Great picture-perfect coastal towns – You haven’t visited Maine until you go to one of the quintessential fishing towns complete with weathered buildings, lots of lobster traps piled on docks, and seagulls circling overhead. Top towns to visit are Camden (quaint-city), Rockland (lots of lobster and the Farnsworth Museum is a must if you love art), and my favorite: Deer Isle. Deer Isle is perfect for a road trip – you don’t need a ferry to get there as there’s a bridge and it’s off the beaten path, so you can explore it in relative peace. If you visit all of these towns, you could spend anywhere from two days to five taking full advantage of the coast.
  • Apple picking in an orchard – There are lots of u-pick orchards around, so it’s just a matter of 1) where you are, 2) that it’s a weekend (they’re almost never open for apple picking during the week), and 3) it’s one of those snap-crackle crisp fall days that just have to be spent outside (and out of your car). One orchard I can recommend that’s fairly central is Thompson’s Orchard in New Gloucester. Not only can you pick your own apples, they have wonderful fresh baked goods (ooh, yeah, love the warm cider donuts sprinkled with cinnamon sugar!), horse-drawn trailer rides, fresh apple cider, a pumpkin patch, and they’re open seven days a week all day! A whole day spent apple picking is a wonderful fall activity, but you can also just stop on your way to pick up some goodies at a farm stand.

New Hampshire and Vermont Road Trip Ideas
Best time: All of October

Fall foliage

As we’ll be winding between these two states, these road trip ideas fall under one heading. The state will identified after each town/destination for clarity.

  • Lake Winnipesaukee, NH – Take back roads over to get on NH Rt. 11 from Alton up to the lake. This beautiful route will introduce you to the largest lake in NH and some wonderful leaf peeping. This is a popular summer destination, but, just like in On Golden Pond, sometimes a lake’s greatest moments are when the summer’s crowds have left and all you can hear are the loons and the wind in the trees. Stay to the right after Glendale and head over to Meredith, a charming town with plenty of great shops, a gallery, and the excellent Inn & Spa at Mill Falls (if you feel like splurging). One to two days should be a perfect amount of time to spend here.
  • Woodstock, VT – This is one of my favorite towns to spend a morning or afternoon strolling around, and you get there on back roads (Rt. 104/Highway 4), which makes it even better. There are lots of great shops and this is the home of one of my favorite Vermont restaurants, Bentley’s.
  • Highway 4 from Woodstock to Rutland, VT – This winding country road is fantastic year round, but when you factor in the fall leaves, it becomes magical. The route winds through the mountains and alongside rushing rivers, punctuated with ski resorts and quaint Vermont towns. Definitely stop in Killington to ride the gondola and see the astounding views from high up on the mountain. If you spend the morning in Woodstock, you could spend the afternoon driving this route, stopping for a gondola ride, and staying at an inn overnight so you can truly enjoy the next item on this hit list.
  • Maple Sugar and Vermont Spice, Mendon, VT – This little wooden restaurant serves up fantastic fluffy pancakes with their own syrup (they make it right there on the premises). The cozy environment, maple syrup making equipment, and shop specializing in all-things-maple add up to a must-see on your leaf peeping trip. It’s on the way to Rutland along Rt. 4, so it’s easy to fit in.
  • Keene, NH – The pumpkin is New Hampshire’s state fruit, and nowhere is it celebrated with more enthusiasm than at the annual Keene Pumpkin Festival. This festival is one day long and always held in October, the specific Saturday selected each year. If you want to stay in town, book ahead – lodging disappears so quickly, it’s almost spooky (just like a Halloween ghost)! This is one of the coolest fall festivals in New England – the annual massive jack-o-lantern display is so amazing that the orchestrated illumination at dusk alone is reason enough to experience this fest.


Massachusetts Road Trip Ideas
Best time: All of October

  • Salem, MA – Haven’t had enough Halloween? Salem is the ultimate Halloween destination as well as a just-plain-charming old New England town. Even if you’re not a Halloween nut, if you’re interested in history, this town has a doozy of a past (the famed witch trials) as well as a notable American author (Nathaniel Hawthorne’s House of Seven Gables is fascinating). The Witch House museum may sound like something out of a fairy tale, but it’s really a great museum detailing life in colonial Salem – one of my favorites. You can spend 2-3 days here.
  • Marblehead, Ma – Salem is a bit more bustling, and the surrounding towns aren’t quite as charming (okay, they’re pretty rough), but if you head out to Marblehead, you’ll be able to visit a wonderful little town off the beaten track that hasn’t changed much over the years. This is a perfect short stop along the way to Boston. I’d make it a morning where you can explore the small downtown, have a nice lunch at the Barnacle (pony up to the bar and relax, it isn’t a fancy restaurant), and then head on to Boston.
  • Boston – Leaf peeping in Boston? No, not in the way you’d think. It’s really just the ease of exploring the town, the classic experience of watching crew races on the Charles, wandering Harvard "Yaad", and walking the Freedom Trail that make it a must on a fall road trip through this area. It’s truly a great city. If you don’t have a lot of time, just go on one of the Duck tours – these great tours are on both land and water – and take in every notable sight in the city.
Want some more road trip ideas to continue your fall road trip? Jump on Rt. 44 and head southwest into CT on this road trip itinerary (reverse the order of sights/stops and you’re good to go).

Other great fall road trip ideas on the East Coast include traveling on the famous Blue Ridge Parkway and traveling through the Brandywine Valley (one of my all-time favorite road trips for the fall). Although the Brandywine trip was designed for the spring, it's just as, if not more, wonderful in the fall.

I love road tripping in the fall – there’s no better way to sample all the amazing beauty of this season than on the road!

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