Seven Fall Days in New England

In mid-October, our little family spent a dreamy seven fall days in New England. I realize this post is late for the current year (2022). It’s been a busy few weeks. However, if you’re reading this in the future this is the perfect itinerary to make the most of a New England fall vacation. We visited Vermont, New Hampshire, Maine, and Massachusetts over the span of seven days. It’s a reasonably packed itinerary, but easily adaptable.

Vermont: Days 1-3

We started our week by flying into Boston and driving to Brattleboro, Vermont. This was mostly a travel day, but we did manage to meet my cousin and her daughter who is just about the same age as our girl. We went apple picking, out to lunch, and then just let the girls run around in an open field for a few hours. An easy way to get the wiggles out before a few long car days. We also managed to sneak in a quick hike to see Retreat Tower just outside Brattleboro. It’s an easy walk with free parking just across the road.

We arrived at our hotel, Pinnacle Lodge, rather late so we pretty much all crashed out for the evening. However, I did notice that we were right next to a lake and I just knew it would be misty and gorgeous in the morning. So, naturally, I dragged us all out of bed at the crack of dawn. It didn’t disappoint.

From here, we started picking our way up Vermont Route 100. This north-south byway runs along the eastern edge of the Green Mountains. It’s known as the skier’s highway, and along the way, you’ll find some of the best hotels, restaurants, and shopping. Of course, in the fall, this is prime leaf-peeping territory.

We picked our way from Brattleboro to Stowe over the course of most of our second day. Notable stops include Ungrounded Coffee (maple latte all day), Green Mountain Sugar House (their ice cream is fantastic), and several classic Vermont delis. Just before midday, we embarked on another relatively easy hike called Deer Leap Overlook. This 2.2 out-and-back hike is fairly steep in parts but not overly technical. I can also confidently say that altitude sickness absolutely plays a factor in my ability to comfortably hike uphill. We did a climb in Durango in August and I was dying. Living at sea level problems I suppose. We ended our day in Stowe, Vermont, with dinner at American Flatbread. I know everyone says they have the best pizza, but these guys might actually mean it. Amazing.

We began our third day in Stowe, a quintessentially tiny, gorgeous, New England town. It also happens to be the home of Ben & Jerry’s Ice Cream. We decided against a visit on this trip, but it was fun to drive by and see the headquarters of one of my favorite large ice cream brands. Instead, we satisfied our sweet tooth at Cold Hollow Cider Mill which boasts the best apple cider donuts ever. As someone who frequently jokes about apple cider donuts tasting like yesterday – IYNYK – I can promise you, these are amazing. The best I’ve ever eaten by a wide margin.

While in Stowe, we also stopped to snap some photos of the famous little white church nestled in the trees. Simply gorgeous.

Vermont Hotels:
Pinnacle Lodge
Fairfield Waterbury Center (Marriott)

New Hampshire: Days 3-4

Continuing the third day of our trip, we left Stowe and Vermont behind for New Hampshire. While the leaves were still gorgeous, there was a noticeable shift in scenery. The mountains became much more extreme as we transitioned away from the Green Mountains and into the White Mountains. These dramatic beauties include the dramatic Flume Gorge State Park and trail*. This striking natural gorge is 800 feet long with granite walls rising 70-90 feet high. At their narrowest, the walls are only about 12 feet apart. The path is a 2-mile loop that takes you directly through the gorge, and then up above it for stunning views. We happened to visit on a rainy day, but it certainly didn’t make the hike any less gorgeous.

For our second day in New Hampshire, we did something completely different: the Conway Scenic Railway. This is something Sean and I would probably never do before becoming parents, but here we are. Our daughter is just at the age where trans, plains, and automobiles are all the rage. We figured she’d enjoy an hour-long train ride through the valley.

Well, honestly, her reaction was a bit mixed. Unfortunately, it was still raining so the windows of the train completely fogged up making it hard to see anything. Additionally, we moved fairly slowly so she was nearly lulled to sleep. It was a lovely relaxing morning, and I would definitely recommend visiting if you’re in the area.

New Hampshire Hotel:
The Lodge at Jackson Village
*Please note: Flume Gorge is open seasonally. 

Maine: Days 4-5

After our little train ride, we departed for Maine. I’ll be honest, Maine was the state I was probably least enthusiastic about when we were planning the trip. I’m not sure why. I think I was concerned about rushing the leaf peeping, but I can’t be sure. However, I ended up falling head over heels in love with Portland. We stayed at the AC by Marriott right on the water which was instantly entertaining for our daughter. The rain subsided as we drove, so we spent some time wandering before dinner at Highroller Lobster Co. The big draw for this restaurant for us was the option to do lobster roll flights. Yes, please.

In the morning we wandered off the beaten path a bit to visit Little Woodfords Coffee and try out The Holy Donut. Little Woodfords is absolutely worth the walk straight uphill, but approach The Holy Donut with caution. They ruined my life. I’m so furious they aren’t in Maryland. I’m not a donut person, but these oddly savory, cakey, donuts are everything. Their dark chocolate sea salt will change your life.

Before departing, we poked around Two Light State Park on Cape Elizabeth. This part is home to the first twin lighthouses on the coast. Parking is free and easy, and the pathways are fully fenced to keep patrons safe. We also ate a quick lunch in the park at Bite Into Main for a last-minute chowder and lobster roll fix.

Maine Hotel:
AC Hotel by Marriott

Massachusetts: Days 5-7

And now, we take an abrupt turn. Away from gorgeous scenery (to an extent) and drive straight into Salem, Massachusetts. Salem is famous for the 1692 witch trials, during which 200 people were accused, and 20 were put to death for allegedly practicing witchcraft. Today the city pays respect to these fallen townsfolk, as well as leans heavily into the allure of modern witches. There are countless famous landmarks revolving around the witch trials including Proctor’s Ledge, Charter Street Cemetary, The Witch House, and the Salem Witch Museum. Running parallel to history, Salem is full of modern-day witch shops with attractions such as broom-making, tarot readings, aurora photography, crystal charging, and so much more.

Now we went to Salem in October. This was intentional, and we knew it would be ridiculously busy. However, we were there on a Thursday and Friday, and I can say it was much more relaxed on the first day. If you do plan to visit in October, I’d highly recommend mid-week. We didn’t do tons of “typical” attractions such as a walking tour or some of the museums, but we did make a point to visit Proctor’s Ledge, Charter Street, and The Witch House. I did hear tons of good things about several walking tours so I do believe they would be a great addition to your trip. (For the record, we didn’t do one because 1) we are both very well versed on the Salem witch trial history, and 2) we were traveling with an 11-month-old.)

We had originally planned to spend a third day in Salem, but after fighting crowds, on Friday we opted instead to hand out in Boston before catching our evening flight home. Since we had limited time we hit a few main highlights: New England Aquarium, Mike’s Pastry, and strolling the North End.

Salem Restaurant Recommendations:
Gulu-Gulu Cafe
Flying Saucer Pizza Company
New England Soup Factory
Odd Meter Coffe Co.
Brew Box

Our Favorite Salem Shops:
Coven’s Cottage
Cauldron Black
Hive & Forge
Roost & Company
The Good Witch of Salem

Massachussettes Hotels:
The Coach House
Four Points By Sheraton Wakefield

If you’ve made it to the end of this extremely long post, thanks for sticking with me all this way. New England in the fall simply can’t be beaten. A true photographer, foodie, and outdoorsmen’s playground.