New England Fall Road-trip Itinerary: Massachusetts, Vermont, New Hampshire
golden leaves, Mountain hikes, pumpkin patches, warm apple cider, cinnamon donuts – it is AUTUMN HEAVEN here.
I still can’t believe it took me this long to experience New England during autumn (and just New England overall?!?). All I have to say is, I fell in LOVE. If you’re looking to chase fall foliage + plan a little road-trip, MUST add this one to your list.
This might be the most spontaneous trip we’ve ever done (J & I and our good friends Jules and Trey). Booked our flights + one hotel room the night before, then booked the rest of our stays once we arrived. We didn’t really have a reason for this other than just wanting to get away and soak up this cozy season elsewhere (if you’re from Florida, you understand me!!!). Although I would love to someday experience a picturesque cabin in the woods (these are mostly booked months––if not a year in advance), I truly love the spontaneity that comes with not planning anything at all.
There are of course a few pros & cons when it comes to not planning:
Pro: Peak fall foliage doesn’t happen at the exact same time every year, so if you don’t have a stay booked way in advance, you have the freedom to drive to wherever the peak colors happen to be best in that moment and not fear that you will miss it.
Con: Fall is crazy busy in the Northeast USA. So availability and accommodation prices can be a little tricky. This just means you’ll have to go on this trip with a more open mind and be okay with less cute stays. :)
Since our road-trip was very last minute and only 4 nights/5 days, we didn’t have enough time to explore all of the states. So, we chose Massachusetts, Vermont & New Hampshire!
Boston, Massachusetts
Before diving into the itinerary, I do want to mention that we did have to take a COVID test before our flight. We flew into Boston, Massachusetts which requires you to provide a negative COVID-19 test result that has been administered up to 72 hours prior to your arrival in the state.
Day 1: Boston
We flew JetBlue Airways from Miami to Boston and arrived early morning. We felt very comfortable and safe flying this airline as they made sure to leave every other seat empty and take proper precautions amidst everything going on with COVID. As soon as we landed, we met with Jules & Trey, jumped into our car rental and began our mini road-trip!
Since we only had a little over one day in Massachusetts, we were really keen to visit:
Salem, Massachusetts
A small historic town just 35-40 minutes north of Boston – known for it’s witch trials from 1692. You don’t need much time to explore Salem (it can be fully enjoyed in a few hours at most), so we drove out here to spend half a day, grab a small bite and walk around.
Although I loved seeing all the cute homes, I can’t say I fell in love with Salem. We all weren’t too crazy about our visit here. But if you’re into visiting witch houses, doing ghost tours or wandering through a cemetery (especially during Halloween) - then this is definitely a town to visit!
WHERE WE STAYED
After a first half day in Salem, we drove back to Boston to check into our hotel.
Since we booked our Boston stay the night before arriving, staying at the Wyndham Boston Beacon Hill was a great and simple option (2 bedroom for $130 total!).
WHERE WE ATE
Late breakfast/early lunch bite at Brew Box - a small cafe in Salem.
Drove back to Boston and had dinner at Regina Pizzeria (1000% recommend)
After dinner, we had beers & oysters at Bell in Hand - the oldest tavern in America!
Day 2: En route to Stowe, Vermont
We woke up extra early to soak up our last morning in Boston and strolled through the dreamy historic neighborhood of Beacon Hill (pictured below). The most picturesque cobblestone streets lined with Victoria brick houses & antique lanterns.
Breakfast: we had a quick bite at 3 Little Figs before hitting the road!
Journey from Boston, Massachusetts to Stowe, Vermont:
If you’re driving directly, it’s about a 3 hour & 15 minute drive. It took us 4 hours because we had a couple of stops planned in between!
First stop: Equinox Valley Farm – Manchester, Vermont
There’s a pumpkin patch, corn maze, greenhouse and WARM APPLE CIDER WITH FRESHLY BAKED APPLE CIDER DOUGHNUTS. Still dreaming about these!!!!
Next stop: Sleepy Hollow Farm - Woodstock, Vermont
Just 10 minutes from the Woodstock village is Sleepy Hollow Farm located on Cloudland Road. This is an iconic property in Vermont known for its picturesque farm, gardens, cabins, woods and ponds. It’s a dreamy view with all the foliage- but since it’s a private property, you can only take photos!
I do have to say it’s very touristy so I would maybe suggest going early morning or close to sundown (hoping it’s not as packed as it was during the day).
Driving through Woodstock was my favorite. A charming little town filled with back country roads & old rustic farms. It’s a real life postcard. 🥰
Final stop: Stowe, Vermont
WHERE WE STAYED
We arrived in Stowe around 8pm, so we went straight to check into our Bed & Breakfast, ordered in dinner and called it a night. I have to say this was my favorite stay from the trip – a quaint family-run inn Butler’s House located in the heart of Stowe. If you’re looking for a cute stay, great location and an incredible cafe downstairs, this one is a gem :)
Dinner: ordered take out from The Bench. Other options in town: lunch at Green Goddess Cafe or dinner at Piecasso. Although we didn’t get a chance to try these, they were highly recommended!
Day 3: En route to White Mountains, New Hampshire
We decided to have a slow morning in town before heading out to New Hampshire.
Breakfast: Butler’s Pantry!!! The family that owns this charming house also have a small cafe downstairs serving the yummiest home cooked breakfast. The menu is so simple yet so incredibly delicious. The banana pancakes are a MUST try!
2 hour drive from Stowe to White Mountains, New Hampshire
Our first stop was Artists Bluff - a short (but a bit steep) hike that takes you to a dreamy overlook of Franconia Notch State Park. You face both the beautiful Echo Lake & Cannon Mountain. This was such a sweet spot to soak up allllll the fall foliage.
*We parked across the street at the Echo Lake parking lot and then just walked across the street to the Bald Mountain Trailhead. The trail can be a little confusing, just make sure to stay right! This is the quickest way to get to Artists Bluff (if you go left, it’ll take you to the Bald Mountain trail).
After the hike, we drove 15 minutes to Lincoln, New Hampshire.
Lunch: we stopped on the side of the road for some mid-day coffee + sandwiches at Half Baked & Fully Brewed.
Next stop: Rocky Gorge Scenic Area
Located in the White Mountain National Forest, Rocky Gorge is a beautiful waterfall where you can walk along the Swift River and get views of the Falls Pond.
To get to Rocky Gorge, make sure you drive through the Kancamagus Highway (the most magical drive through the White Mountains). You’ll find heaps of beautiful road-side views and pull-outs for dreamy photo opportunities!
Dinner: After exploring New Hampshire for the day, we hit the road back to Stowe, Vermont for some dinner + beers at Idletyme Brewing Co.
Day 4: Last day in Stowe – back to Boston
We woke up at 5am to head back down to Boston (3 hour drive).
WHERE WE STAYED
Found a last minute deal at Courtyard Boston Downtown where we spent our last night in the city.
WHERE WE ATE
Lunch: It rained ALLL day so we decided to cozy up in our hotel room, took the best afternoon naps and ordered ramen + boba from Amateras (nothing better than this on a rainy day!!).
Dinner: Crudo (yummy sushi) was located in Boston’s historic “Little Italy”, a really cute area to walk around and then we headed over to Mike’s Pastry for dessert!
Day 5: Bye Boston!
Breakfast: We woke up and went straight to grab morning brekkie + coffee at Tatte Bakery (MUST VISIT if you’re in Boston!!!). This spot was highly recommended & it was a true gem. Good coffee, avo toast and heavenly pastries :)
Luckily, it was all sunshine on our last day! So we just walked around, created content, soaked up our last moments in the city and before we knew it was lunch time.
Lunch: we HAD to end our New England road trip with some lobster rolls + clam chowder from the Quincy Market - a historic market filled with tons of foodie stops, pubs, shops, artisan stalls and more.
MY TIPS:
If you’re planning a last minute getaway, make sure to track the fall foliage map of that year with peak dates and destinations (there are tons online but the Farmer’s Almanac is a good source).
If you have the option to stay at a Bed & Breakfast, do it! Their intimacy and connection to the local scene can give you such a different perspective of the town or city you’re staying in.
This goes for all of my travels when it comes to finding yummy food spots (aside from local recommendations). DOWNLOAD YELP! I’m an avid yelper and I can def say I’ve found some of the most incredible eats through this app. It’s also the easiest when you’re on the road & looking for something nearby.
If you can, take more time off to extend this road-trip. I do wish we could have spent more days exploring the little towns & beautiful landscapes here- buuuut this just means we’ll have to come back next year hehe.
Lastly…go on your road-trip with an open mind and SPONTANEOUS heart. You really do end up finding the sweetest spots in the most unexpected places (especiallllly on an autumn trip like this!).
PIN ME FOR LATER
