Plan a New England Fall Road Trip to Less Obvious Spots

I don’t care where you’re from but fall just hits differently in New England. We’ve been all over the world during the autumn months and they must put something in the dirt here, honestly.

If you time things right, you may just be able to follow the leaves from north to south. How magical does that sound?

What I’m sharing with you here is our two-week New England fall road trip itinerary from our adventures in New England.

Some of the stops here are destinations you wouldn’t expect on fall foliage trips throughout New England. We had cost and efficiency in mind, but I’ll make suggestions on alternatives and offer the more popular stops where appropriate, too.

Where to Go in New England in the Fall

Don’t listen to the others. You have SO many options for excellent leaf peeping in New England. You don’t need to head to the usual spots for photoshoots among the crunchy leaves and delicious autumn treats.

If I had to choose our favorite state for fall colors in these parts, though, it’d have to be Vermont. It just seemed so much more vibrant than the others, but that could also have something to do with our timing.

Keep in mind that this guide is limited to New England fall road trips, as per your search request. You’ll see some jokers including states like New York in their roundups, which is fun but inaccurate.

New York isn’t part of New England, so you won’t see Lake Placid represented here. I’ll cover all of the six New England states on this road trip.

The Best Time to See New England in the Fall

The best time to see peak foliage in New England is when the leaves start changing colors. This sounds vague on purpose. The timing changes somewhat from year to year.

Mid-September through the end of October is usually the best time to see New England fall colors.

The itinerary you’ll read about here happened around the start of October into the middle of the month, and the colors were spectacular.

How to Spend Two Weeks in New England in the Fall

You can spend your two weeks in New England like this:

• Day 1: Woodstock, Vermont
• Day 2: Stowe, Waterbury, and Montpelier, Vermont
• Day 3: Lyndon, Vermont
• Day 4: Burnham, Maine
• Day 5: Acadia National Park, Maine
• Day 6: Bangor, Maine
• Day 7: Rockland, Maine
• Days 8-9: Portland, Maine
• Day 10: Portsmouth, New Hampshire
• Days 11-12: Boston, Massachusetts
• Day 13: Providence, Rhode Island
• Day 14: New Haven, Connecticut

How to Plan a New England Road Trip

The best place to start your New England road trip is Vermont, arguably the most spectacular state when it comes to fall foliage. You could spend all of your time here and get your fall foliage fix if you don’t want to drive a ton.

How you get there depends on where you’re starting. We were driving from the Finger Lakes region of New York to kick things off.

New England can be expensive to visit, especially if you want to live off of lobster rolls for the duration of your visit. 

Visiting in the fall in particular on a New England itinerary can really test your budgeting skills. It can cost a pretty penny to stay in the most well-known towns around New England if you don’t plan far in advance. 

We booked our accommodations a few months ahead of our own trip, and it really wasn’t enough time. The highlight, though, was experiencing the smaller, less popular stops along the way.

Day 1: Woodstock, Vermont

Driving from New York, we stopped in Woodstock on our way to where we’d be staying the next little while: Lyndon, Vermont. I’ll get into that in a minute, but first, Woodstock.

This one is billed as the quintessential New England town. That also means the leaf peepers will be in full effect if you’re there for fall road trips in New England.

That’s OK. Embrace it. Crunch along some leaves. It’s a beautiful place. Woodstock highlights include:

• Downtown Woodstock: Start here to get yourself situated in Woodstock. You can stroll around to go tchotchke shopping at the boutiques or walk off of Main Street for the most delightful architecture. Find all of your favorite pumpkins.
• Sleepy Hollow Farm: If you want to peep at leaves against rolling pastures, head to Sleepy Hollow Farm. This is one of the most photographed rural spots in the country and has been here since the 1700s.
• Sugarbrush Farm: Sample Vermont maple syrup and over a dozen different kinds of cheese at this third-generation family farm. The cheeses here come with a special wax coating to lock in all of that cheesy goodness.
• Marsh-Billings-Rockefeller National Historical Park: This is Vermont’s only national historical park, but it’s a beauty in the fall. Take a tour of the Marsh-Billings House and find The Pogue, a pond tucked away in Mount Tom Forest.
• Middle Covered Bridge: This scenic bridge on Union Street was the first covered bridge built by the state of Vermont after 1889. It replaced an 1870s-era iron bridge that had been condemned for several years. I’m here for all the facts, people.

The small town of Lyndon was our base for Vermont, and we’d recommend it to see some excellent Vermont highlights within a short drive of town. It was also quiet and mostly void of leaf peepers, which pleased me very much. 

We’d also highly recommend it to see some excellent Vermont highlights within a short drive, including access to magical Dog Mountain for the pet owners amongst you.

Some of you may prefer to keep things efficient, and you have options for accommodations in Woodstock proper.

The Woodstocker B&B would be my pick for a return visit. If you’re traveling as a couple, this one is adults-only. Guests love the fresh brioche in the mornings and warm cookies in the afternoons. It’s the little things.

Use the map below for more options:

Day 2: Stowe, Waterbury, and Montpelier, Vermont

It sounds like a lot, but I promise it can be done. All three towns are in close proximity to one another. If you meet the crowds in Waterbury that we did, the much-talked-about whimsy of the place will die down a bit and cause you to flee elsewhere.

Start in Stowe. As soon as we left this town, I knew I had to go back. Brian loves to ski, so a repeat visit to check out Stowe Mountain Resort is certainly a possibility. I like to lounge, so a visit to Stowe during any season is a possibility for me.

If you have more time, check out my guide to Stowe. Otherwise, don’t miss these Stowe highlights:

•  Trapp Family Lodge: If you love Austria, you’ll love this property. You can hit several trails around the property for panoramic views, snack on brats at the Bierhall at von Trapp Brewing, or even stay at the lodge.
• The Alchemist Brewery: Many beer lovers make the pilgrimage to Stowe to try Heady Topper, one of the most drinkable double IPAs you’ll find anywhere. If you’re visiting on a warm day, get yourself a can to enjoy in one of their Adirondack chairs.
• Gold Brook Covered Bridge: You may see this one labeled as the Stowe Hollow Bridge or Emily’s Bridge on your map apps. They’re all the same and they’re all lovely.
• Mount Mansfield: If you’re visiting up to about mid-October, you can drive to the top of Vermont’s tallest peak on the Auto Toll Road. The parking area at the summit sits at 3,850 feet, so the panoramas are lovely up there.
• Stowe Cider: I had a sour candy-infused Gummy Bears hard apple cider here that sounds like it should be a mistake, but it definitely wasn’t. Try a flight for a taste of some more unique or classic flavors. My fave was the High & Dry.

Waterbury is next and just a short drive from Stowe. It was quite thick with the leaf peepers by the time we got there mid-afternoon, but that’s what you get when you’re all cute and offering people all of the fall things.

This place has hot cider, hot cider donuts, all of the pumpkin things, and cheese. For a quickie visit, don’t miss:

•  Cabot Farmers’ Store: Sample all the Vermont cheddar you can handle and buy a novelty T-shirt while you’re at. I mean, that’s what I did, but do whatever strikes your fancy.

• Cold Hollow Cider Mill: When I was talking about all of the cider things, this is the best place in Waterbury to make that happen. If you’re traveling in a pair, have your honey stand in line for their legendary cider donuts while you browse the rest.
• Vermont Beer Collective: Formerly called Craft Beer Cellar, this Waterbury beer shop is the spot if you’re looking for that one craft beer you had in New England back in the day. Their selection is stellar.
• Prohibition Pig: Delicious meats and a good variety of craft beers are all allowed and welcome at this Waterbury eatery and brewery. Come for drinks or stay for smoked wings, brisket, or their epic whole hog group experience.
• Ben & Jerry’s: I’m not telling you to go to the grocery store and pick up some ice cream treats for your travels. This is the Ben & Jerry’s factory. It’s the only one you can tour in the country and is home to the hilarious Flavor Graveyard.

Montpelier was so close to Waterbury that we had to pop by for a visit if only to check out the state capitol.

Here are some highlights in Montpelier with a few in nearby East Montpelier for good measure:

• Vermont State House: The golden dome on this capitol building is worth the price of admission. That admission is free, by the way, so if you want a guided tour you can make it happen at no charge.

• Hubbard Park: If you’re already visiting the state house, visit this 194-acre green space next. It’s a short walk just north of the capitol building to perfect picnic spaces and hiking trails if you want to stretch your legs.
• Coburn Covered Bridge: If you’re really into covered bridges, you should just move to Vermont because this state is just lousy with ’em. This one is the only surviving 19th-century covered bridge left in East Montpelier.
• Bragg Farm Sugarhouse & Gift Shop: It’s time to get a taste of pure and yummy Vermont maple syrup. This farm has been operating for eight generations. If you’d like to go on a guided tour, they’re free.
• Morse Farm Maple Sugarworks: I can’t just leave you here with just one maple syrup operation running for eight generations, can I? Here’s another. If you didn’t get enough of that sweet stuff at Bragg Farm, have yourself a few more samples.
• The Quirky Pet: Folks with pets won’t want to miss this place. It’s a pet shop essentially run by two mops and two kind humans who helped me pick out some bones and treats for Kimmy.

You have some options for accommodations tonight, but if you want to be in on the action for tomorrow, stay near Lyndon just as we did.

This country cottage in Lyndon is where we stayed on our trip. The layout was a little wild, but it was spacious and in a country setting that really fit the trip’s vibes.

If you don’t mind spending a bit more to stay in Stowe because you’ve fallen in love with the place, use the map below:

Day 3: Lyndon, Vermont

If you’re staying near Lyndon, you’re off the beaten path. Take advantage of that. Lyndon is a short drive to some pretty fantastic spots, namely Dog Mountain and Lake Willoughby.

I have a full love letter/blog post on Dog Mountain that you can peruse at your leisure, but if you’re traveling with your pup, it’s basically a must. It’s a wonderland for dogs, and the only leash requirements are inside the gift shop.

Lake Willoughby is another must-stop if you’re already in Vermont’s Northeast Kingdom. It’s been compared to Norwegian fjords for a reason and likely won’t be one of the state’s most impressive hidden gems for long.

Fun fact: This dramatic landscape was carved out by glaciers. I’m telling you, this is one of those comparisons that tracks.

Stay another night in or around Lyndon or return to your hotel in Stowe. If that’s the case for you, you’ll just have an extra hour of driving tomorrow.

Day 4: Burnham, Maine

You’ll have about four hours of driving today to Burnham if you stayed in or around Stowe. This will be your home base for adventures in and around Bar Harbor.

Why not just stay in Bar Harbor, you ask? Well, traveling regularly and in a regular fashion sometimes (er, usually) means you’re traveling on a budget.

It’d be great to stay near Acadia National Park if you plan on visiting as we did, but you have to plan well in advance to find anything within a short drive of the park.

Note: I’m talking like, many months in advance, tacking on a few additional months for good measure if you’re visiting in the fall.

It’s also expensive, especially if you’re traveling in the fall. I’m talking VERY expensive. If you’re good with that and would rather prioritize efficiency over cost, I feel you. I’ve been there, and I get that. 

We were working with more time, though, so that’s how we came to be a little further out. If you’re in Burnham as we were, take it easy today after the drive. Stroll Unity Pond or visit the Field of Dreams. 

Fun fact: No, it’s not that Field of Dreams. You’ll need to travel to Iowa for that. It’s still not bad.

I watched that movie well into adulthood, by the way, and it is creepy and weird as heck. Does anyone else concur?

If you want to follow our itinerary to the letter, we stayed at this secluded Burnham retreat. You’ll need to drive to anything you need, but that’s the point of seclusion, right? I’d highly recommend this one.

You may also just want to stay in Bar Harbor. Use the map below for those:

Day 5: Acadia National Park, Maine

We were about 90 minutes outside of the park, so we hit the road early with our pup in tow to make the most of that hike.

If you’re visiting with your furry friend, check out my guide to making a similar day trip to Acadia happen. I include dog-friendly trails and where they’re not allowed, too.

Whether you’re traveling with a pup or on your own, Acadia is a hikers’ paradise with some of the best views anywhere in the United States.

Don’t miss these trails and attractions if you’re here for all of that:

• Bass Harbor Head Light Station, more casually known as the Bass Harbor Head Lighthouse, isn’t the most photographed lighthouse in Maine. It’s still worth a stop if you’re early on in your lighthouse exploration. Visit it on Mount Desert Island.
• If you’re here for the leaves and not the hikes, the Park Loop Road is 27 miles worth of scenic driving through some of the best views in the park. There are all kinds of short loop hikes that start along this path if you’re looking to stretch your legs.
• Reach Cadillac Mountain with either a steep 3.1-mile ascent to the summit or a scenic drive complete with pullouts along the way. We did the drive up and didn’t feel like we missed out on anything.
• Stroll the Ocean Path Trail to quintessential Acadia attractions like Sand Beach, Otter Cliffs, and Thunder Hole. Thunder Hole is named for the waves that crash against the rocks here. On ideal days, the spouts can go as high as 40 feet.
• If you’re traveling with a pup as we were, the Wonderland Trail is much less crowded than the trail I just mentioned and just as fun. Make sure your pup can handle rocky areas and a little scrambling if you go that route.

Day 6: Bangor, Maine

Stephen King fans won’t want to miss this one. The town was the home of the horror author for decades until he decided to split his time between his other home in Maine and a Florida home.

Note: You can still visit the mansion’s gates as I did, likely with other fans giggling about the wrought iron accents. Yes, that’s a red balloon in the photo.

For a full day of fun, check out a few more Bangor highlights:

• Paul Bunyan Statue: This 31-foot-fall statue is here to tell all who visit Bangor that the town was his place of birth. That’s what locals say anyway. He’s very tall, a little bit creepy, and an easy stop while in Bangor.
• Mount Hope Garden Cemetery: If you love a good cemetery, don’t miss the second-oldest garden cemetery in the country. Oh, and it was also a filming location for Pet Sematary. (Did you know that was spelled that way?!)
• Hollywood Casino: If you want to try your luck at some card tables or whatever else people do at casinos, head to one of only two casinos in Maine. Can you tell I prefer spending my money elsewhere? I don’t judge you, though.
• Penobscot Narrows Bridge: You’ll need to travel about 30 minutes south of Bangor. Connect to the Fort Knox Historic Site and the Penobscot Narrows Bridge Observatory on the other side.

Day 7: Rockland, Maine

This is peak coastal Maine right here and the part of the state that made me consider Maine as a potential new home for us. Yes, there will be lighthouses and plenty of them.

For the best of Rockland, check out these highlights:

• Rockland Harbor Trail: Embrace those maritime vibes with this stroll along Rockland Harbor. If you’re visiting in the fall as I did, expect vibrant foliage on the side that isn’t the waterfront.
• Jess’s Market: If you’re not sure where to get started for delicious seafood in town, start with this fish and lobster shop. Visiting on a chilly day? They’ll likely have chowder for you to slurp up, too.
• Marshall Point Lighthouse: This lighthouse is about a half hour south of Rockland in Port Clyde, but it’s one of the most picturesque scenes you’ll encounter in this part of the country. It was also featured in Forrest Gump, so run right over, k?
• Owls Head Lighthouse: This stunner was built in 1825 and has since become one of the most popular lighthouses in MidCoast Maine. It’s a short 10-minute drive to this one from downtown Rockland, so I think I’m cheating even less with this one.
• Rockland Breakwater Lighthouse: If you haven’t navigated breakwater with a dog yet, this is a great place to test out your pup’s mettle. Watch your step — the breakwater is nearly a mile long here! — and head all the way up to the lighthouse.

We stayed in Owls Head, Rockland’s neighbor, as our overnight in the area. Both are adorable and great places to stay overnight.

If you want to stay in Rockland proper, use the map below for some options:

Days 8-9: Portland, Maine

You’re only a few hours to Portland from here. Portland is Maine’s most populated city, the cultural heart of the state, and my preferred Portland. While you may know how much I love coastal Oregon and the other Portland, Maine just hits differently. 

Take some time to enjoy those (hopefully) sunny autumn days in Portland and the best of the Maine city’s attractions: 

• Portland Head Light: This historic lighthouse is in Cape Elizabeth, but that’s just a 15-minute drive from downtown Portland. You’ll drive through South Portland to get to Portland Head Light, one of the state’s most photogenic spots.
• Old Port: Start in this charming historic district and fall in love with Portland just as we did. The Old Port boasts a great dining and live music scene on top of that adorable cobblestone.
• Eastern Promenade: This harbor-side stroll is two miles from end to end, but you can do as much as you please. This promenade comes to us courtesy of the same folks who brought us Central Park in New York and the Boston Commons.
• A Piece of the Berlin Wall: There is an actual piece of the Berlin Wall right here in Portland. Find the trio of slabs at Long Wharf, a harbor that’s worth your time with or without a visit to this literal piece of history.
• Bug Light Park: If Portland Head Light didn’t do enough for you, head to Bug Light. This one got its name for its small size, but it’s not the size that matters. It’s how a lighthouse keeper uses their…light? I don’t know. It’s cute.

Once you’re done with the sightseeing, indulge in some of Portland’s best eats. If you haven’t had at least half a dozen lobster rolls yet, grab another at Portland Lobster Company. The outdoor tented bar is a great place to grab a drink and chow down.

Here are a few more food recs as you eat your way through Portland:

• Boone’s Fish House & Oyster Room: Slurp up more oysters with your waterfront dining or opt out as I would with their chowder and delectable mussels. Yes, you’ll want to add more bread.
• Duckfat: If you’re still thinking about the fries you housed on that one trip to Brussels, make a beeline for Duckfat and their Belgian-style frites. They’re double-fried. In duck fat. You’re welcome.
• Eventide Oyster Co.: I’m honestly not the right person to ask about oysters, as I call them the boogers of the sea. Outside of its well-known oyster program, though, this eatery does it up with crab buns, lobster stews, and ceviche.
• Terlingua Restaurant & Market: Portland has incredible seafood. If you’re craving some hot meats — get your head out of the gutter — plan to taste some Maine barbecue at this casual eatery.

Interested in a drink before or after to build that base? Portland’s beer scene is unmatched. Allagash Brewing Company is where you should start.

If you’re planning on crawling to your Portland accommodations, Austin Street Brewery, Rising Tide Brewing Company, and Oxbow Blending & Bottling are all a good time, too.

Stay in Portland for a couple of nights so that you’re able to spend at least a full day sightseeing and another full day eating your way through all of that delectable seafood. We stayed at the La Quinta by Wyndham Portland with our pup in Portland.

We generally love the La Quinta brand when we have our dog along because they don’t slap you with excessive fees and parking is easy. I’d recommend it anyway.

Use the map below for more options in Portland:

Day 10: Portsmouth, New Hampshire

Portsmouth is a lovely place that deserves a day of your time, especially if you’re visiting in the fall when the sun’s still shining and the leaves are crunching. For more on what we did there, visit my guide to this New Hampshire town.

If you don’t want to leave this post just yet, here are the Portsmouth highlights:

• Market Square: This is basically Portsmouth’s beating heart. It’s where you’ll find the bulk of the town’s boutique shopping, cafes, and art galleries. They do it up around Halloween with their decor, too.
• Prescott Park: Take in the views along the Piscataqua River with a stroll at Prescott Park. This is also where you’d check out the Prescott Park Arts Festival if you weren’t visiting in the fall.
• The Warner House: This is just one of Portsmouth’s historical homes, but it was the one we chose to visit during our Portsmouth trip. This house is over 300 years old, making it one of the oldest brick structures in New England.
• Memorial Bridge: Want to do something fun? Walk across this bridge. You’ll be in Maine on the other side. Just make sure you don’t time your stroll around the regular bridge lifting.

You’ll need somewhere to stay in or near Portsmouth. We’ve stayed at the Ale House Inn, a historic property that once housed a brewery. It was more than a novelty. This was a fun, comfortable stay with possible deals in the off-season.

Use the map below for more options:

Alternative Ideas for New Hampshire Stops

Now, you may be wondering where the White Mountains and Mount Washington are in this tour of New England, particularly in the fall. Well, those mountains are thick with peepers in October.

You need to book well in advance if you don’t want to spend $400/night on accommodations in and around the White Mountain National Forest.

We just couldn’t do it.

That doesn’t mean you shouldn’t. It’s still firmly on our list, and we plan on returning. Specifically, I imagine myself snapping pics overlooking Crawford Notch State Park and bopping around North Conway on the regular.

Here are a few more items on my New Hampshire bucket list:

• Franconia Notch State Park
• The Conway Scenic Railroad
• Dixville Notch State Park
• Kancamagus Highway
• Lake Winnipesaukee
• Cannon Mountain Aerial Tramway

I know. It’s a lot.

Days 11-12: Boston, Massachusetts

In just two more hours, you’re in Boston.

If you’re flying into New England for less than the length of this itinerary, this is a great hub to choose for some excellent leaf-peeping drives from Boston.

As we have so much to see, I’m only dedicating two full days to one of the best cities in Massachusetts, but you’ll certainly want to come back. 

With more time, you’ll be able to tack on a few day trips from Boston. Salem is all kinds of fun if you’re visiting around Halloween time. Want to have yourself a spooktacular time? I have a guide to visiting Salem in the fall.

Cape Cod is perfect for lovers. I don’t know. I just think about all the mayhem those Kennedys got into on the Cape. 

READ MORE: I have SO many more ideas if you want to hang around Boston. Check out my favorite day trip options.

If you’re staying in Boston proper, you’ll have a lot to do to fill your time. If you’ve never done the Freedom Trail, you can spend at least a full day doing that. On top of the historical attractions along the Freedom Trail, don’t miss:

• Boston Common: This is a great place to lounge and people-watch if your legs are tired from the Freedom Trail. It’s also the oldest park in the United States.
• Isabella Stewart Gardner Museum: Visit this art museum for the art, but stay because of its courtyard. You’ll feel like you’re anywhere but Boston and that’s purposeful. This place was modeled after a Venetian palace.
• Museum of Fine Arts, Boston: This museum isn’t just a jewel of Boston’s art scene. It’s well-regarded as one of the best art museums in the country. It boasts the only permanent exhibition of ancient coins in the U.S. and a Claude Monet collection.
• Harvard Square: Visit Cambridge for the home of Harvard University and practice those Good Will Hunting accents you pull out after a good brewery. Start with Harvard Square, the town’s arts and eats center.
• Boston Breweries: Speaking of good breweries, Boston has plenty of them. Trillium Brewing Company, Aeronaut Brewing Co., and Harpoon Brewery, the local staple, are the top stops I’d recommend.

We stayed in Lexington on our last visit to Boston, but I’d probably just stay in Boston proper if I was to do it again. The traffic in the city can get intense and if you’re short on time, you’ll want to be in the thick of it all.

Just book well ahead of your travel during fall foliage time, as things can get expensive in Boston.

Use the map below for options in Boston proper:

Day 13: Providence, Rhode Island

Providence is an excellent city to spend the day. For whatever reason, it hasn’t arrived as a popular fall foliage road trip destination, so you’ll compete with fewer leaf peepers while you’re there. 

If you’re still not convinced, I have a post on all of the reasons you should make a trip to Providence happen.

Interested in the highlights? While in Providence, don’t miss:

• The First Baptist Church in America: This is the oldest Baptist church in the United States. Check out the exterior at the very least unless you’d like to time a visit during a worship service.
• Trinity Brewhouse: I had a hard cider here that tasted like apple pie that caused me to melt into my booth. I also still think about the incredible mural this place has over the bar. It’s a version of The Last Supper with dead musicians.
• Brown University: Walk the campus or head straight to Thayer Street. This is where both locals and Brown coeds go for casual eats and some of the city’s best ethnic cuisine.
• West Side Diner: This classic diner has been operating out of a diner car on this spot since 1947. It was just known as Poirier’s Diner back then. Order yourself a patty melt and feel yourself go back in time.
• The Museum of Art, Rhode Island School of Design: You’ve probably heard of this one by its shortened name: RISD. The museum’s impressive exhibits touch on a little bit of everything, including fashion. It’s a must-see while in Providence.

If you have more time to explore Rhode Island, don’t miss Newport. It’s very different from Providence, just from a point of fanciness.

I put together a guide to its mansions, one of the most popular things to do in Newport if you want an idea of how fancy things get around here.

If you only have time for one Newport mansion, by the way, make it The Breakers. The old Vanderbilt pad is the most popular for a reason.

Providence offers more budget-friendly stays than Newport as you look to book your overnight at this point. I’ve stayed at the Residence Inn Providence Downtown on stays in Providence. What it lacked in charm it made up for with charming prices.

Use the map below for some more options:

Day 14: New Haven, Connecticut

New Haven quickly became one of my favorite New England cities on our fall trip. That prestigious university adds quite a bit of cultural heft to any visit there, with several of the country’s top museums all in one place. Already into it? I’ve got a New Haven guide. 

At the very least, you’ll want to eat your way through the best New Haven pizza.

Spoiler alert: It was Pepe’s for me. While Pequod’s in Chicago will always hold a special place in my heart, New Haven-style pizza is also quite special. 

If you want the quick ‘n dirty highlights on New Haven, don’t miss:

• Harkness Tower: This is a symbol of the city and a symbol of Yale University. Tours to the top are available during certain times of the year, so check that out if you want the best view of the campus.
• Yale University Art Gallery: See works from van Gogh, Monet, and Rubens without paying a dime to do so. Expect to spend a few hours at this one. It’s also my favorite rainy-day activity in New Haven.
• PEZ Visitor Center: This one is technically in Orange, but it’s close enough that I wouldn’t get upset by another travel blogger sending me outside of the city. It’s a no-brainer whether you’re traveling with kids or just PEZ-loving adults.
• Marjolaine Pastry Shop: Reward yourself for all that learning with some high-end sweets. We visited on a gloomy day, so I had to get myself a decadent hot chocolate. It was a “yes” on the whipped cream, too.
• Yale Center for British Art: Start at the gallery above, but continue with this art museum, the largest collection of British art outside of the United Kingdom. The halls inside are impressive all on their own.

We spent a full week in New Haven because it was one of the more budget-friendly stays in New England during our fall travels. I wouldn’t recommend where we stayed, so you won’t see it here. It was the size of a shoe, not even the full shoe closet.

If you’re lucky enough to be overnighting in New Haven, check out the map below:

With More Time on a New England Road Trip

If you want to stay in New England for a bit longer, I don’t blame you. New Haven is a great base for day trips to other Connecticut fun. Julia Roberts fans won’t want to miss the place that gave us Mystic Pizza just under an hour from New Haven.

READ MORE: If you’re a nerd for romantic comedies, you’ll want to visit Mystic. Use my guide!

Hartford is another great day trip, particularly if you’re a fan of Mark Twain. It’s home to the Mark Twain House & Museum. Their excellent tours will tell you all about the life of Twain and his family in that house from 1874-1899. 

We booked one of their living history tours. Twain’s former maid, costume and all, told us about all of the gossip she overheard while living in the house with his family. It was very entertaining and very well done.

With more time in Hartford, visit the Harriet Beecher Stowe Center and both capitol buildings. There’s the current Connecticut State Capitol and Connecticut’s Old State House. Both are worth your time.

Art fans won’t want to miss the Wadsworth Atheneum Museum of Art. It has a little bit of everything, whether you’re a fangirl for the Impressionists or were obsessed with ancient Egypt as a kid.

This is where I leave you, a full two weeks after you began your New England fall road trip. We continued traveling south for the winter from here, driving down into Delaware, Maryland, and West Virginia along the way.

You can certainly extend your time at any point during your trip. I could bop around Maine indefinitely, to be honest.

A New England fall road trip is worth the effort.

New England is already one of the most beautiful regions in the U.S. Add the vibrant hues of fall and it’s all almost overwhelming.

It’s what made me seriously consider moving to New England until I started thinking about winters, too. I’d love to return to see more of states like New Hampshire doing their thing in the fall. It’s truly the best time to see this part of the country.