It’s that time of year when the world turns orange, and by orange, I mean pumpkin everything. I’ve been a pumpkin fan long before it became trendy. Growing up in the Midwest, it’s practically in my DNA. But living in California now, my love for autumn feels a bit out of place. Each year, I find myself longing to escape to somewhere chilly in October to fully embrace the fall season and get my seasonal fix.
Michigan is always a great choice with its apple orchards and pumpkin patches, not to mention the stunning fall foliage up north. Utah and Lake Tahoe, closer to California, have also made the list. But nothing compares to the ultimate fall destination…NEW ENGLAND.This is the Mecca for autumn lovers, and trust me, nothing compares.
Last fall, we made the pilgrimage to New England to see the majestic mountains blanketed in vibrant colors. It was a refreshing escape, fully immersing ourselves in everything autumn. My travel companions, as always, were my husband and our two daughters. Our journey focused on three states: Massachusetts, Vermont, and New Hampshire.
Starting in Boston, where there’s a direct flight from California, we spent one afternoon exploring the city (a full Boston travel post is coming soon). Usually, I enjoy dining at Lucca’s in the North End, but this time we opted for Fillipo Restaurant. It’s a charming, old-style mom-and-pop shop with pictures of celebrities on the walls and classic Italian dishes. The kids loved the penne, and the lobster ravioli was a hit. A stroll through the historic North End brought us to our favorite cannoli shop, Mike’s. Just a heads up, it’s cash-only, but there’s an ATM on site. We also walked the Freedom Trail, taking in the historic sites along the way. We grabbed a few slices of pizza from super famous Regina’s Pizza, some of the best New England pizza there is. We stayed at the Courtyard Boston Downtown/North Station, a convenient choice for our short stay. Renting a car at the airport is a must if you plan on exploring and taking in all the sights.
The next morning, we were off to Salem, just a 30-minute drive from Boston. I recommend taking the scenic route along the water. Our first stop was the Witch House. A quick tip: tickets go on sale the day of the visit at 10 AM on Eventbrite, so grab them fast. The guided tour inside is educational, but even if you miss out on tickets, the exterior is still worth a photo. Hocus Pocus fans, Allison’s house is just a minute away! Next, we visited the Ouija Board Museum, a quirky little shop with historic Ouija boards that the kids found intriguing. Then, we stopped by The Salem Witch Museum, which offers a 30-minute show about the history of the Salem Witch Trials. The kids found it both educational and entertaining. Salem is a charming town, especially during the Halloween season, with food trucks and themed events all over. Don’t miss Essex Street, the main shopping street where you’ll find Halloween characters and festive treats. Of course, we visited all the Hocus Pocus sites and indulged in some delicious, albeit unhealthy, snacks.
Our next destination was Woodstock, Vermont. Pro tip: book your stay at the Woodstock Inn well in advance—I booked eight months ahead, and it was worth it. If they’re fully booked, try The Shire Woodstock, Windsor Mansion Inn, or On the River Woodstock, all great alternatives. The Woodstock Inn offers excellent food, service, and cozy rooms with beautiful decor. My kids loved the billiards room in the basement. We enjoyed a delicious fall-themed dinner at the hotel’s restaurant, with highlights like squash soup and maple cake with ice cream.
Woodstock is a small, welcoming town, even with the influx of tourists. Do note that Wi-Fi can be spotty in these rural areas. We started our day at Springbrook Farm for a cheese-making tour (call ahead for availability). Although we missed the cheese-making session, we still toured the facility and met the farm animals, including cows, chickens, and pigs. The views were breathtaking, and the cheese was excellent. We also stopped at Taftsville Bridge for photos along the river. There are many historic bridges in this area to always opt to stop and take in the views and some photos.
Next, we visited Sugarbush Farm, where they make maple syrup. You can explore the maple trees, meet farm animals, and let the kids play on the playground. The shop offers everything maple syrup-related. The drive through the mountains was stunning, with the fall foliage adding to the experience. Although we couldn’t visit Sleepy Hollow Farm due to road closures, we loved the nearby Billings Farm and Museum. The museum offers insights into the area’s history and farming practices, and the kids enjoyed learning about the animals and even meeting some live turkeys. We indulged in ice cream, hot cider, and donuts at the farm and relaxed in the kids’ library, a perfect break.
Back in Woodstock, we strolled through town, exploring shops and finding the best ice cream at Woodstock Scoops—maple-flavored, of course. I had the maple waffle with, maple swirl ice cream, and maple chips on top. The next morning, we visited the Norman Williams Public Library and Yankee Bookshop, where the kids spent hours in the children’s section. We also took photos at Middle Bridge and Pleasant Street, lined with charming picket fences and pumpkins.
Our last stop in Woodstock was VINS (Vermont Institute of Natural Science), where we enjoyed the forest canopy walk and the raptor exhibit. The girls got to see the rapture feedings up close and learn a lot about the way they live. On our way back to Woodstock we stopped in Quechee and found a small apple orchard called Whitman Brook Orchard, and the owners were so nice to let us pick apples even though they were about to close. I wanted the kids to experience apple picking in a real orchard.
The next day, we visited the Ben and Jerry’s factory for a tour of how they make ice cream. I purchased tickets in advance, so be sure to do that. It’s about an hour’s drive from Woodstock, and the scenic drive is lovely. The factory is very kid-friendly, with a park and a “dead ice cream flavor” graveyard. The tour was lively, and the kids enjoyed tasting samples along the way. In the end, we received a generous sample of ice cream, and then, of course, we bought a bunch of ice cream and souvenirs. We then headed to Stowe for a gondola ride, but the weather didn’t cooperate. It was cloudy, and the visibility was poor, so we decided not to wait in line for an hour to see nothing. We refunded our tickets and instead took a smaller gondola ride down to the resort, where we had dinner at Alpine Hall inside The Lodge at Spruce Peak—a cozy spot. Since the weather wasn’t in our favor, we didn’t get to explore Smuggler’s Notch or the town, but I highly recommend visiting those spots if you have the chance.
On our way back to Woodstock, we stopped at The Von Trapp Family Lodge, which features charming Bavarian architecture and is nestled at the top of a mountain. As we descended the mountain, we spotted a beautiful herd of Highland cattle, which looked picturesque against the mountain backdrop.
You could end your trip here and drive back to Boston, or continue on to the White Mountains in New Hampshire. The drive along the Kancamagus Highway offers breathtaking leaf-peeping opportunities and leads to the Omni Mount Washington Resort. This historic hotel, nestled atop the mountains, is a beautiful spot to relax. The hotel offers various dining options, an indoor pool, a game room for kids, and even a laundry room for guests. The kids enjoyed a carriage ride around the property, and we soaked in nature with a round of golf on their beautiful course. The Omni’s history is fascinating, and the hotel even has a Gold Room where the historic Bretton Woods Agreement was signed. In the evening, we roasted marshmallows at the outdoor fire pit. If you missed the gondola ride in Stowe, you can still catch one here at the resort which takes you up to a few dining options.
After soaking in all the autumn vibes, you can either drive back to Boston Logan Airport, about three hours away, or head to Portland, Maine, just two hours away. Either route offers scenic views to complete your fall adventure.