Boston to Maine: 5-Day New England Fall Road Trip Itinerary

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Fall is my absolute favorite time of year, and what better way to celebrate it than by sharing my epic 5-Day New England Fall Road Trip Itinerary with you? Living in Tampa, we don’t get to experience much of that crisp air and vibrant foliage, so heading up north always feels like such a treat!

And let me tell you, New England is the ultimate destination for a dreamy fall road trip—it’s like driving through a live postcard! From cider mills to charming coastal towns and those famous fiery leaves, this itinerary will have you falling head over boots for autumn.

This itinerary will take you from Boston to Portland Maine, making stops along the way that showcase some of these unique cities and towns! We did our trip at the end of October and juuust missed peak foliage, but Mother Nature still came through with plenty of gorgeous colors. Pro tip: Peak foliage timing can vary each year, so definitely use a foliage tracker to plan your ultimate fall adventure.

New England Fall Road Trip Itinerary

Day 1: Drive from Boston to Maine with a Pitstop in Salem, Massachusetts

Once our flight landed in Boston, we decided to kick off our trip by heading straight to Maine and saving Boston for our final day. The drive from Boston to Maine is a breezy two hours, but trust me, you’ll want to make a stop in Salem along the way. It’s only 40 minutes from Boston and has the perfect blend of history, charm, and spooky vibes.

Salem is famously known for its ties to the 1692 witch trials, where 20 people were tragically tried and executed. These days, the city embraces its eerie reputation with Halloween festivities and fascinating attractions. Plus, Salem is home to historical gems like the House of the Seven Gables, a 1668 landmark immortalized by Nathaniel Hawthorne’s novel of the same name.

We only had a few hours to explore, but Salem left such a strong impression that it quickly became one of my favorite stops on this entire New England fall road trip. Here are a few things to do in Salem if you’re planning a visit:

Things to Do in Salem, Massachusetts

• Snap pics at Hocus Pocus filming locations: It’s a classic for a reason! Most of the filming spots are easy to find, so try to hit a couple while you’re here. Here’s a list of where you can find all the spots.
• Visit The Witch House (The Jonathan Corwin House): This is the only structure still standing with direct ties to the Salem witch trials. Adult admission is just $9, and it’s open daily from 10 AM to 5 PM. Meaning if you have a mid-afternoon flight, this may be the first thing you want to do.

• Stroll through the shops: Downtown Salem is a lovely to wander through, with quirky shops, unique souvenirs, and even a few places to get a tarot reading (yes, I had to try it!).
• Grab a bite at The Roof: This rooftop bar serves up tacos, burritos, and bowls alongside fun cocktails. We even got to enjoy it under a hauntingly perfect full moon!
• Dive deeper into the history: If you have extra time, check out the Salem Witch Museum to learn more about the witch trials ($16.50 admission). You can also join one of the walking tours, like the Voodoo, Vampires, and Ghosts Walking Tour or the Salem Night Walking Tour, for a deeper dive into Salem’s spooky side.

After soaking up the magic of Salem, it’s time to hit the road again. Your next stop is Portland, Maine, which is just over an hour away. We stayed at the Holiday Inn Portland – By the Bay, and it was the perfect place to rest up for the next day’s adventures!

Day 2: Portland, Maine

Portland, you beauty! This coastal gem totally lived up to the hype, and I’m already dreaming of a summer return. Portland has that perfect mix of small-town charm with big-city vibes, making it the ultimate destination for anyone who loves amazing food, stunning scenery, and unique experiences.

With its cobblestone streets, craft breweries, and drool-worthy seafood, Portland is a feast for both your taste buds and your sense of adventure. It’s like a playground for foodies, nature lovers, and culture enthusiasts. For our visit, we turned the day into a self-guided foodie tour while soaking up the charm of this vibrant seaside city. Here are some must-do’s for your Portland itinerary:

Things to Do in Portland Maine

• Start your morning with Bard Coffee: Walking to this cute coffee shop was a dream thanks to the crisp fall weather. Their coffee was amazing, and though the indoor seating wasn’t open, it worked out perfectly for a stroll with a steaming cup in hand.
• Indulge at The Holy Donut: Just around the corner from Bard Coffee is this Portland classic serving up potato donuts (yes, really!). Flavors like pomegranate, blueberry lemon, and honey lavender make it hard to choose, so why not grab a few? (It’s so funny to me that donuts seem to be just as much of a craze in Portland, Oregon as they are in Portland, Maine.)

• Visit the Portland Head Light: This iconic lighthouse is the oldest in Maine, and WOW, it’s a showstopper. Located in Fort Williams Park, you’ll find picnic spots, scenic cliff walks, and even lobster rolls from Cousins Maine Lobster. This is one of the best things to do in Portland and a must for your 5-day New England fall road trip itinerary!
• Lunch with a view at Luke’s Lobster: What’s a trip to Maine without a lobster roll? Luke’s serves up the classics, and their waterfront views make it all taste even better. Don’t skip the chowder—it’s just as divine.

• Sip your way through local breweries and distilleries: Oxbow Blending & Bottling is a must for beer lovers, with an impressive draft list and even some unique wines. And right next door is Hardshore Distilling, where you’ll find gin so smooth you’ll be tempted to sip it straight (or enjoy it in a creative cocktail).
• Snack on Duckfat‘s famous frites: Conveniently located near Oxbow, Duckfat’s Belgian-style fries are hand-cut, twice-fried in—you guessed it—duck fat, and absolutely irresistible. The perfect snack to fuel the rest of your Portland adventure!

Day 3: New Hampshire | Conway, Lincoln, + White Mountain National Forest

The drive from Portland to the White Mountain Forest is just over two hours, but the good part is it’s two hours of pure eye candy! New Hampshire rolled out the ultimate red (and orange and yellow) carpet for us with its incredible fall colors. We found ourselves pulling over every chance we got to soak it all in—because, honestly, how can you not?

With limited time on this trip, we packed in as much as possible, but we barely scratched the surface of what New Hampshire has to offer in the fall. Here are a few highlights to inspire your adventure:

Things to Do in New Hampshire

• Cruise the Kancamagus Highway: This 34.5-mile stretch through the White Mountain Forest is an autumn wonderland. Scenic overlooks, vibrant foliage, and endless photo ops make this a must-do for your 5-day New England road trip itinerary.
• Stop at Lower Falls: A popular scenic spot along the highway, Lower Falls offers parking, a picnic area, and even restrooms. In warmer months, people can be spotted taking a dip in the watering hole—it’s that dreamy.
• Snap pics at Albany Covered Bridge: Just minutes from Lower Falls, this picturesque bridge with a babbling stream beneath and vibrant foliage all around is straight out of a postcard.

• Dinner at The Common Man in Lincoln: End your day with a feast. Their Nantucket Pie—a heavenly combo of shrimp, scallops, haddock, and Maine lobster baked in a rich lobster cream sauce—is pure indulgence and worth every bite.
• Hiking options galore: Though we didn’t have time for hikes, New Hampshire’s trails are calling us back. Some popular ones to explore include:
  • Diana’s Baths: A short, 1.3-mile hike to a cascading series of small waterfalls.
  • Flume Gorge: A 2.2-mile loop featuring a dramatic natural gorge.
  • Smugglers Notch State Park: A variety of trails perfect for every adventure level.

We spent the night in Lincoln at the Holiday Inn Express & Suites Lincoln East – White Mountains. It was cozy, affordable, and came with breakfast—perfect for fueling up before another day of leaf-peeping magic. Plus, saving a few bucks on food means more room in the budget for New England goodies!

Related read: This southeast USA road trip itinerary, Utah road trip itinerary, and Arizona road trip itinerary are three other great fall road trip options!

Day 4: Vermont | Stowe, Waterbury, and Burlington

Vermont in the fall? Absolute perfection. Stowe, Waterbury, and Burlington are must-visit spots if you’re chasing those quintessential autumn vibes. Stowe, less than two hours from Lincoln, greets you with lush forests and rolling hills. From there, it’s a quick 20-minute jaunt to Waterbury, a charming town with a rich history and scenic valleys. Another 30 minutes beyond Waterbury lands you in Burlington, where lakeside views and Ben & Jerry’s history await.

Stowe, Waterbury, and Burlington are all great places to visit in Vermont in the fall! Stowe is a little less than 2 hours from Lincoln and has lush forests and rolling hills. A quick 20-minute drive from Stowe gets you to Waterbury which has charm, history, and beautiful valleys.

Just another 30 minutes outside of Waterbury you’ll find yourself on the eastern shoreline of Lake Champlain in Burlington, where Ben & Jerry’s originated.

Things to Do in Vermont

• Explore Stowe’s beauty: Take a drive and soak in the scenery. For a bit of adventure, tackle the Percy Farm Corn Maze. Don’t be surprised when they ask for your number in case you get lost—this maze is no joke! But hey, we escaped in just 30 minutes, so you can too.
• Savor cider in Waterbury: Stop by Cold Hollow Cider Mill for their famous cider donuts, cider slushies, and hard cider. Fall never tasted so good.

• Discover Burlington’s charm: Wander through Church Street Marketplace, a pedestrian mall packed with over 100 shops, restaurants, and lively events. We treated ourselves to an incredible lunch at Leunig’s Bistro (the beef bourguignon is a must) and rounded out the day with drinks at Foam Brewers, Fiddlehead Brewing Company, and Shelburne Vineyard.

Somehow, we managed to cover three cities in one day without feeling rushed. It’s proof that when the vibes are right, you can accomplish more than you think—note to self the next time I’m struggling with my to-do list. We did only get just a taste of them (literally and figuratively), but I feel like what we did and saw were some of the best things to do in Vermont.

To wrap up the day, we grabbed dinner at Molly’s Restaurant in Hanover before heading to our hotel, the Holiday Inn Express & Suites Manchester-Airport. It was a 2 ½-hour drive from Burlington and just under an hour from Boston, where we’d end our adventure the next morning. A perfect mix of productivity and play!

Day 5: Boston

The grand finale of our New England fall road trip! Boston is a city bursting with history, charm, and endless things to see, eat, and do. Even after two trips, I feel like I’ve only scratched the surface of what this iconic city has to offer. Here are some of my favorite things to do in Boston and a few things still on my list for next time!

Things to Do in Boston

• Explore Beacon Hill: This dreamy neighborhood is straight out of a storybook. Stroll along its brick-paved streets lined with Federal-style and Victorian row houses, and don’t miss Acorn Street—one of the most photographed spots in the city. Its cobblestone charm is a rare find these days!
• Snap a pic at Fenway Park: Baseball fan or not, Fenway is a must-see. It’s the oldest major league ballpark still in use, and even standing outside gives you a sense of its history. Bonus points if you catch a game!
• Tour the Samual Adams Brewery: Dive into Boston’s beer scene with a visit to this iconic brewery! Take a tour to learn about their brewing process, enjoy samples of their craft beers (including exclusive taproom-only offerings), and soak up the laid-back vibes of the Beer Garden.
• Visit the Boston Public Library: Located in Copley Square, this library is a jaw-dropper. Whether you’re a book lover or just appreciate stunning architecture, it’s worth a visit. It’s hands down one of the most beautiful libraries I’ve ever seen!

• Go whale watching: If you’re in Boston between April and October, this is a must. Hop aboard a high-speed catamaran for an epic whale watching tour. Keep your eyes peeled for humpback whales, fin whales, and playful Atlantic white-sided dolphins. It’s a magical experience!
• Walk the Freedom Trail: Dive into Boston’s rich history on this 2.5-mile trail featuring 16 iconic sites, like the Paul Revere House, Boston Common, Old State House, and Old North Church (where you can tour the crypt!). Guided tours are super affordable and add so much depth to the experience.
• Shop at the Prudential Center: Treat yourself to some retail therapy at this gorgeous indoor shopping center. Don’t miss Eataly for a foodie paradise! Next door, you’ll find Copley Place, another stunning shopping destination.

• Explore Cambridge: Just across the river, Cambridge is packed with charm. Wander through Harvard’s historic campus, grab a bite at The Asgard, or level up your night at a speakeasy. Roxy’s Arcade (hidden in a grilled cheese shop with arcade games!) and Brick and Mortar are both unique spots to check out—just don’t be surprised if you have to hunt a little to find them!
• Hop on a Duck Boat Tour: Want to see Boston from the streets and the water? These iconic tours in renovated WWII amphibious vehicles take you through the city’s highlights before splashing down into the Charles River for breathtaking skyline views.

• Check out VERSUS— A super fun arcade bar! This spot combines retro games, neon vibes, and a menu of cocktails and bites that’ll keep the good times rolling. Perfect for a night of nostalgic fun!
• Eat at Legal Sea Foods— Hands down, the best (and only) whole lobster I’ve ever had! Picture this: lobster stuffed with shrimp and scallops, paired with a creamy lobster bisque packed with chunks of lobster. Mouthwatering, right? With multiple locations across Boston, it’s a must-visit for fresh seafood lovers.
• Grab coffee from Trident Booksellers & Cafe— Cozy vibes and comfort food collide! This charming cafe is ideal for rainy Boston mornings, serving up delicious coffee, breakfast, and bookshop magic. Come for the coffee, stay for a page-turner!

Are you ready to experience this epic Boston to Maine New England fall road trip itinerary?!

If you are looking for a fall road trip, New England is one of the best. From Boston to Portland, Maine and each stop in between has so much to offer. From the cobblestone streets of Boston to the postcard-worthy colors of New Hampshire and the cozy cider mills of Vermont, every stop is sure to be amazing!

This trip gave me all the fall feels—crisp air, warm apple cider, and those ridiculously stunning autumn landscapes that make you wonder if Mother Nature is trying to show off (spoiler: she is). I’d do it all over again in a heartbeat—preferably with an extra day or two!