I have wanted to travel to the northeast during the fall for as long as I can remember. I was so excited when I got the opportunity this fall to do so with one of my best friend’s Taylor from @brown.eyed.flower.child We always have the best time together and this trip did not disappoint. It’s absolutely beautiful up there during fall!
Day 1
Fly into Boston Massachusetts BOS airport.
I of course got the earliest flight out of Dallas so I could get there with plenty of time. Honestly, you could stay in Boston for a night if you didn’t want to drive much or if you wanted to see some of Boston. We decided we were gonna go ahead and head to New Hampshire.
We arrived in New Hampshire checked in at The Valley Inn in Waterville Valley, NH. The location of this hotel is perfect to enjoy all kinds of outdoor activities. From biking and golfing to skiing in the winter. They have so much to offer right close to the hotel! Walking distance to the town square and 5 mins from Waterville Valley Ski area. The bright fall trees around the property were stunning along with the view from our bedroom window.
We went to grab dinner at The Covered Bridge Farm Table. A lot of places close early so make sure to check times before going.
Where to stay- The Valley Inn in Waterville Valley
Where to eat- The covered Bridge
Drive time- 2 hours
Day 2
This was going to be our first full day so of course, we wanted to make the most of it. First, stop breakfast. We were going to Polly’s Pancake Parlor but the wait was 1.5 hours so we decided to pass. I’m sure this place is amazing! It had awesome reviews but I would recommend getting there when they open.
So we opted out of breakfast and headed to Littleton for lunch. We ate at Littleton Freehouse Taproom & Eatery which was great. Taylor and I shared a cider & craft beer flight which was perfect.
Now it was time to hike. We headed to the Artist Bluff Hike it’s a 1.5-mile loop hike with incredible fall foliage! Do this one counterclockwise. I also recommend hiking boots as well. It can be muddy in spots if it has rained. This hike you will be climbing a little but it’s a pretty short area! The views are just stunning. We missed the peak by a couple of days but it was still gorgeous!
After our hike, we wanted to experience and drive along the Kancamagus Highway. It’s one of the top scenic highways in New Hampshire so if you are there at peak fall time this is a must. It takes about an hour from start to finish and keep in mind there are no gas stations or stores along the way. Also, not much cell service either so plan accordingly. I know there are stops you can make along the way with waterfalls. We didn’t have time since we knew it was starting to get dark out.
Now it was time for dinner we stopped at Matty B’s Mountainside Cafe. The pizza is awesome. Taylor and I did the pizza deal. You get 1 large pizza, a salad, and a bottle of wine for $30. Sign me up! Also, the pizza was amazing so if you are in the area make a stop in.
Where to eat
Breakfast – Polly’s Pancake Parlour
Lunch- Littleton Freehouse Taproom & Eatery
Dinner- Matty B’s Mountainside Cafe
Where to stay- The Valley Inn in Waterville Valley
Total Drive time – 4 hours 15 mins
Day 3
Now it was time to make our way to Vermont. We decided to just grab something quick for breakfast and head on our way. Made it to Woodstock, Vermont. We parked and explored the cute town of Woodstock. Honestly, you have to make a stop here this town is adorable and is the perfect fall town. The Woodstock inn is so beautiful and the mums are just stunning. The perfect photo spot.
After exploring Woodstock we decided we want to go to a Cidery. We drove to Cold Hollow Cider Mill which is close to Stowe, Vermont. Of course, I had to try the apple cider donuts and they didn’t disappoint. Then we both got flights of cider we picked and enjoyed a while here at the amazing place. Also, you can eat here as well.
On our way to the Cidery, we saw Ben and Jerry’s so we decided we had to stop here on our way back to Woodstock. It’s right down the road from the cider place so it’s so convenient. It was the perfect snack along the way. We both love Ice cream. The views here were also just beautiful.
Now it was time to head to our Lodge for the night. Mountain Meadows Lodge in Killington. It’s about 30 mins from Woodstock. The mountain meadows lodge is located just 5 miles from the Killington K1 gondola. So the perfect place to stay in the winter as well for skiing. This 26 room lodge sits along part of the Appalachian trail and they even have Daisy the sweet dog that will go with you on your hikes while there. They had s’mores sat up for us by the fire and just the beautiful views alone were just so inviting. The hosts were truly amazing and made you feel right at home. This is a place you absolutely don’t want to miss.
Now it was dinner time we headed to 506 Bistro and it was the perfect end to our day. The food was incredible.
I got the panini for my main
I got the lava chocolate cake and Taylor got the pumpkin pie
After dinner, we headed back to Mountain Meadows Lodge and made s’mores by the fire and had a glass of wine, and talked to others staying at the lodge. It was the perfect ending to such a great day. If we had more time here we would have done a hike with Daisy! I would recommend staying at least 2- 3 nights at Mountain Meadows Lodge
Where to stay – Mountain Meadows Lodge
Where to eat
Breakfast – Mon Vert Cafe
Lunch – Cold Hollow Cider Mill
Snack – Ben & Jerry’s
Dinner – 506 Bistro
Total Drive Time – 5 hours
Day 4
Now it was time to head to Massachusetts but first, we wanted to stop at the famous Sleepy Hollow Farm to snap some pictures! It’s so beautiful there. Now it does get crowded but we parked a little past where a lot of people take pictures and it was the perfect spot and not a lot of people around us till we were about to leave
We arrived at The Red Lion Inn in Stockbridge, Massachusetts. This is a historic inn and it’s one of the few American Inns that have operated continuously since before the 1800s. It’s always fun staying at the historical places and learning some history about them. This is a very popular spot to stay in Stockbridge and we enjoyed it there. They have an awesome heated pool and hot tub as well. They are located very close to many restaurants, hiking, bars, and shops.
Now it was time for happy hour and some relaxing. We stopped for drinks at Mooncloud which was great they also have awesome charcuterie as well. We decided we wanted to check out a winery while we were in this area so we headed to Balderdash Cellars. They had live music and a fun atmosphere in a beautiful setting. Now it was time for dinner. We ate at the Morgan house it was great. We tried to go to 51 Park Restaurant & Tavern first but the wait was 1.5 hours. The food looks amazing there so definitely recommend just arriving early. We ate and then headed back to The Red Lion inn to get some rest.
MoonCloud 
MoonCloud 
Balderdash 
Balderdash flight 
Morgan House Dinner
Where to Stay – The Red Lion Inn
Where to eat/ drink
Breakfast – Mountain Meadows Lodge
Drinks – Mooncloud
Winery- Balderdash Cellars
Dinner
Total Drive time
4 hours 22 mins
Day 5
We got up ate breakfast at the Red Lion Inn and then We decided we wanted to get some more hiking in so we found a great trail before our next stop. We did the Hickey, Peeskawso, and Mohican Monument Loop. It’s combining a few different trails into one but it was the perfect hike with incredible views! I would say it’s a moderate trail just because there are rocks and climbing. I recommend hiking boots. It’s 2.6 miles with a 685ft elevation gain. Totally worth it. One of my favorite trails I’ve hiked.
Now it was time to make our way to our last stay. The Miraval Berkshires Resort & Spa. This is somewhere you come and don’t leave. The resort has so much to offer I promise you are not going to want to leave. They offer so much from yoga to hiking, swimming, cycling, ax throwing, cooking classes to much much more. They also have an absolutely amazing spa. It’s truly an experience and so relaxing. This resort is a place you come to relax and disconnect from the world. A place that inspires everyone to create a life in balance. They are a digital device-free resort. Their mission is for you to experience a place free from distractions and gives each guest permission to 100% unplug. They do have certain areas designated for technology if needed. I loved this about this resort. When we live in a world full of everyone depending on their phones it’s so nice to step back and reconnect without distractions.
We got to our room after checking in and our luggage had already arrived at our rooms.
We then headed to get facials. This experience was truly amazing. The best facial I’ve ever had. Just a stunning spa as well. Truly so relaxing.
Then we headed to our room I freshened up while Taylor headed to a yoga class. After she got back it was time for our cooking class. This was such an amazing experience and the food was 10/10! Just incredible. Below is what had during cooking class.
Kale Apple Caesar Salad 
Butternut Squash Fritters 
Barley Kimchi Faro, green beans and Jalapeño glazed trout 
Blonde over maple Greek yogurt with strawberries
We decided we wanted to try some more food they had to offer in the dining room and have a drink to finish our day off
Now it was time for bed. When I tell you this in the most amazing bed and bedding I’ve ever slept in just trust me. We thoroughly enjoyed relaxing and unwinding in the beds we each had.
Where to stay – Miraval Berkshires Resort & Spa
Where to eat – Miraval provides meals, snacks, smoothies, and non-alcoholic beverages for their guest
Total drive time
18 mins
Day 6
Wake up call came early at 6 am for our 7 am cycling class. Honestly what better way to start your day! It was so refreshing and I truly loved it.
After cycle class, we went to have breakfast and some fresh juice/smoothies. Breakfast was awesome.
We, unfortunately, had to go home today. Our time here at The Miraval Berkshires was more than incredible. I promise you are sure to not be disappointed while staying here. It’s everything you could imagine and so much
Courtyard area At the Miraval 
I was flying out of Newark back close to where Taylor lives so she drove me to the airport. There are other airports nearby as well just find what works best for you.
Total drive time
3 hours 15 mins
All in all, we had an incredible time on our New England road trip! I will definitely be back. I will say I recommend 2 nights minimum at each town. Just so you can experience the places and all they have to offer to the fullest.
I am happy to answer any questions you might have. Always feel free to email or dm me.
Much love,
Hannah
