And just like that, it was time for our third annual mother–daughter fall foliage trip to New England. It blows my mind how quickly this little tradition has become one of the highlights of my year.
As a Texas girl at heart, I’ll never get over the magic of true seasons. Every October when Mama and I arrive and those leaves are glowing in fiery reds, golden yellows, and deep oranges, I feel like I’ve stepped straight into a postcard. Photos never do it justice. It’s pure magic in person.
This year, we kept things simple. Instead of racing through new towns, we decided to go back to our favorites from past trips, with one new stop that’s been on our bucket list since the very beginning. It was a shorter loop, but somehow felt fuller like coming home to places we’ve fallen in love with, while still getting the thrill of discovering something new.
Here’s how our 5 day itinerary looked:
Day 1: Stowe, VT
Day 2: Woodstock, VT
Day 3: Woodstock, NH
Day 4: Kennebunkport, ME
Day 5: Boston, MA
Day 1: Stowe, Vermont
After landing in Boston, we drove straight to Stowe, a cozy ski town turned leaf peeper’s dream, nestled in the Green Mountains. Out of everywhere I’ve visited in New England, Stowe always manages to charm me most. Even though it’s touristy, there’s a reason people flock here in the fall. The village is so picturesque it feels like a movie set.
Mama hadn’t been with me the very first year, so this stop felt extra special.
Stay:
- Airbnb right in the village
- Splurge option: The Lodge at Spruce Peak (luxury lodge with ski-in/ski-out access and spa vibes)
Must Do:
- Smuggler’s Notch Drive – a winding mountain pass carved between cliffs, with foliage that frames the road in the most dramatic way. It’s one of those drives where you want to pull over at every bend.
- Spruce Peak Gondola – in just a few minutes you’re whisked up the mountain with sweeping views of the valleys. At the top, there are easy trails that even “non-hikers” (aka me and Mama) can enjoy.
- Village Stroll + Black Cap Coffee – Stowe’s downtown is a row of historic buildings, boutiques, and bakeries. We grabbed lattes at Black Cap, which has the perfect cozy, small town vibe.
- Cold Hollow Cider Mill – one of the most iconic cider mills in Vermont. You can watch cider being pressed, shop their market, and most importantly grab fresh apple cider donuts.
- Butler’s Pantry – a Stowe institution for breakfast. Think hearty pancakes, maple everything, and the coziest start to the day.
- Mad Tom Orchard – if apple picking is on your fall bucket list, this family run orchard delivers. Rows of trees heavy with apples, mountain views in the background.. it’s the quintessential fall activity.
- Cork Wine Bar & Market – a chic little wine bar where we shared plates before diving into the star of the night: their butternut squash, ricotta & lemon zest agnolotti. I’m still dreaming about it.
Day 2: Woodstock, Vermont
If Stowe is charming, Woodstock is pure storybook magic. Known as one of the prettiest small towns in America, it has white steepled churches, covered bridges, and a village green that looks like it was designed for a Hallmark movie.
Stay:
- The Shire Hotel – a simple, centrally located spot right on the river.
- Splurge option: The Woodstock Inn – a luxurious New England landmark with gorgeous grounds, an incredible spa, and restaurants worth visiting even if you don’t stay there.
Must Do:
- Middle Covered Bridge – one of the most photographed spots in Vermont, this 1969 wooden bridge spans the Ottauquechee River right in town. It’s the perfect backdrop for those classic New England fall shots.
- Woodstock Village Stroll – wander the quaint downtown streets lined with boutiques, cafés, and colonial era homes. Every corner feels photogenic.
- Au Comptoir – a chic little cocktail bar that brings Parisian flair to a New England town. Perfect for pre-dinner drinks.
- Prince and the Pauper – a fine dining staple in Woodstock for over 40 years. Cozy, candlelit, and the perfect spot for a mother daughter dinner.
- Sugarbush Farm – tucked just outside of town, this family farm is known for maple syrup and award winning cheeses. You can sample everything (dangerous in the best way) and learn about Vermont’s maple sugaring tradition.
Day 3: Woodstock, New Hampshire
Our new addition for 2023! We chose Woodstock, NH for two reasons: to stay at Lumen Nature Retreat (the chicest collection of tiny cabins in the woods) and to finally score tickets for the Cafe Lafayette Dinner Train, which we’d been trying to book for two years.
Stay:
- Lumen Nature Retreat – Scandinavian inspired cabins and A-frames nestled in the forest, complete with string lights and firepits. A cozy, elevated camping experience.
Must Do:
- Cafe Lafayette Dinner Train – a vintage 1950s railcar turned fine dining restaurant on wheels. The train winds through New Hampshire’s foliage while you enjoy a five course meal. It’s romantic, nostalgic, and unlike anything else.
- Flume Gorge – a natural gorge extending 800 feet at the base of Mount Liberty, with waterfalls, covered bridges, and dramatic rock formations. One of the most scenic (and easy) hikes in the White Mountains.
- Artist Bluff Trail – a short but steep trail that rewards you with sweeping views over Echo Lake and the mountains ablaze with fall colors. It’s one of the most famous leaf peeping hikes in New England.
- Kancamagus Highway (“The Kanc”) – a 56 mile scenic byway through the White Mountains, widely considered one of the best drives in the U.S. during fall. Expect overlooks, waterfalls, and foliage that will make your jaw drop.
- Bear Notch Road & Rocky Gorge Scenic Area – smaller offshoots along The Kanc that are worth the detour for quiet, equally stunning views.
- Sweet Maple Café – a local favorite for hearty breakfasts and lattes. The owner is as warm as the pancakes she serves.
- Mount Washington Cog Railway – the world’s first mountain climbing cog railway. If you have a few hours, riding to the summit gives you 360° views across New Hampshire, Vermont, and even into Canada on a clear day.
Day 4: Kennebunkport, Maine
After three days in the mountains, it was time for a coastal change of pace. Kennebunkport is a historic fishing village turned chic seaside escape, and while it’s gorgeous year round, there’s something extra cozy about visiting in the fall when the summer crowds are gone.
Stay:
- Airbnb in Kennebunk or the surrounding towns. These tend to be more affordable than staying directly downtown, but you’re still minutes away from everything.
Must Do:
- Batson River Brewing & Distilling – a brewery meets restaurant with a stylish, cozy atmosphere. They always deck it out seasonally, and in the fall it’s all pumpkins, plaid, and warm cocktails.
- The Clam Shack – an iconic little shack perched right on the bridge in town. Known for lobster rolls and chowder, it’s the perfect spot for casual, classic Maine seafood.
- Stonewall Kitchen York Company Store – part café, part massive showroom for their jams, sauces, and kitchen goodies. Perfect for brunch and a little shopping.
- Nubble Lighthouse – one of Maine’s most photographed lighthouses, perched dramatically on a rocky island just off the coast. It’s especially stunning at sunset.
- Connor’s Farm – pumpkin patches, corn mazes, and our holy grail: hot apple cider donuts fresh out of the fryer. Finding them warm is rare and trust me, it changes everything.
Day 5: Boston, Massachusetts
We wrapped up our trip in Boston, a city that blends old world charm with bustling, modern energy. Even though it was just a travel day, there’s something about wandering cobblestone streets, grabbing seafood by the harbor, and catching glimpses of fall color tucked between brownstones that made for the perfect finale.
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Final Thoughts
This year’s road trip was shorter, but that’s what made it so special. Instead of rushing, we revisited places that already had pieces of our hearts and actually took the time to linger. Whether that was sipping cider, shopping local boutiques, or just sitting on a bench watching the leaves fall.
Adding Woodstock, NH into the mix gave us just the right sprinkle of new adventure (and the dinner train lived up to every expectation). But at the end of the day, it’s less about where we go and more about who I get to go with. This trip with Mama is truly one of my favorite traditions, and I can’t wait to see where year four takes us.
