New England in a Nutshell: Peak Color & Transportation Bingo
Updated: 5 days ago
This trip started as a 70th birthday celebration for my mom and somehow turned into a full round of transportation bingo.
Over the course of a week in New England, my mom, my sister Angie, and I traveled by plane, coach, train, cog railway, boat, gondola, and enough assorted transfers that it started to feel like we were attempting to use every available method of transportation.
The actual goal was simpler: spend some time together, see New England in peak fall color, ride some scenic trains, visit ridiculously charming towns, and let someone else handle most of the logistics.
There was also bubblegum sparkle toothpaste, mystery Cheerios, memorable commentary, and more mild mayhem than the itinerary advertised.
Letting Someone Else Do the Complicated Part
We booked the trip through Great Rail Journeys, which handled the hotels, most of the transportation, guided touring, and the general logistical puzzle of moving a group of people around New England during peak foliage season. This was my second trip with the same tour company, so I already had a pretty good idea of what to expect.
I love planning trips, but there are times when it is extremely nice to hand over the complicated bits and simply be told, “Meet here at this time.”
The trip began in Boston, then worked its way through New Hampshire and Vermont, with scenic rail journeys, small towns, mountain views, and a truly gorgeous amount of autumn foliage along the way.
TRAVEL TIP 1: WHEN IN DOUBT, OUTSOURCE THE ITINERARY
If planning, spreadsheets, and piecing together fifteen moving parts are not your idea of fun, travel agents and escorted tour companies can be very helpful. Sometimes the best travel hack is letting someone else deal with the logistics.
Boston: Crawling Through History
Our first proper day in Boston began on a bus with Cindy, our local guide, who provided a nearly continuous stream of commentary and made sure we understood we were in Baston. Between that and Boston traffic, we spent a good chunk of the morning crawling through the city at sightseeing speed.
That turned out to be a pretty great introduction. We stopped for photos at Boston Common and the Public Garden, visited the Make Way for Ducklings statues and the Tortoise and Hare sculptures, and headed over to see the USS Constitution.
What really got me, though, was the sheer amount of history packed into the city. Boston Common is the oldest public park in the United States, historic churches and buildings seem to appear around every corner, and whole sections of the city feel like they belong to a much earlier version of America. Trinity Church especially stopped me in my tracks. The carvings, stonework, arches, and layers of architectural detail were incredible, but it was only one piece of the larger effect.
Growing up in the U.S., “historic” can sometimes mean a building from 1923 with a plaque on it. Boston was different. Everywhere we looked were places tied to the earliest chapters of American history, and some of them were among the oldest and coolest things I’d ever seen in the country.
By the end of the day, Boston had made a strong first impression: beautiful, historic, easy to get around, and apparently governed by a completely separate set of traffic rules.
TRAVEL TIP 2: HEED THE WARNINGS, BUT KEEP AN OPEN MIND
Before this trip, I'd heard plenty about Boston's aggressive drivers and "Masshole" reputation. The drivers? I can see where that comes from. The people were a different story. I found the public transportation clean and easy to use, and even watched people go out of their way to thank the bus driver.
Reputations exist for a reason, but they're not ususally the whole story. Listen to the warnings, prepare accordingly, and then let the place show you what it is actually like.
The Revere Hotel committed to the theme. Paul Revere, but make him out of metal bits Trinity Church, casually showing off in Copley Square while the glass towers try to keep up. Founded in 1837, which is frankly showing off by American standards. Copley Square: Boston really does know how to make a fountain look mildly dramatic. Nothing says “Boston harbor” like casually posing with an anchor roughly the size of my MINI USS Constitution, still looking extremely dramatic after all these years. When in Boston: lobster rolls and clam chowda Boston said “lobster,” then really committed to the bit.
New Hampshire: Peak Leaf-Peeping Energy
Leaving Boston behind, the trip started looking a lot more like the version of New England I had pictured in my head: covered bridges, mountain roads, tiny towns, and trees doing their absolute best to show off.
This was also where Kim, our tour manager for the week, really became part of the story. She handled the day-to-day logistics, commentary, and general keeping-the-group-moving duties, while Lorenzo, our driver, somehow made a full-size coach look far more nimble than it had any right to be.
North Conway, our second night's stop, was ridiculously adorable. Not “pleasant little town” adorable. Full Hallmark-movie-set adorable. The kind of place where you half expect someone to announce that the annual cider festival is in jeopardy and only one unexpectedly handsome local carpenter can save it.
We followed the Kancamagus Highway through some of the best foliage of the trip, with mountain views, winding roads, and plenty of photo stops along the way. Kim also made sure we knew we were on the Kancamagus Highway. Frequently. At one stop, this somehow escalated into collecting leaves and rocks in little baggies, because apparently scenic appreciation now comes with evidence bags.
The timing was absurdly good. Some areas were already at peak color, the crowds were still relatively light, and blue sky kept making appearances. Kim said it was some of the best foliage she had seen after years of running trips through the area, and looking around, that did not feel like tour-guide hyperbole.
Even the roadside signs were contributing. We passed a hardware store declaring, “Be the best of yourself unless ur a jerk,” which feels like solid life advice, frankly.
This was also the day my new cozy ghost sweatshirt, a birthday gift from Angie, started collecting compliments from strangers and fellow tour-goers. Apparently New Hampshire was not only delivering on foliage but also providing unsolicited fashion validation. 👻
And looming ahead was Mount Washington, where we were about to discover that sometimes the place famous for terrible weather decides to be extremely cooperative.
New Hampshire autumn showing absolutely no restraint Because apparently New England comes with covered bridges pre-installed Even the structural engineering is charming here Three women, one covered bridge, and absolutely no resistance to the full New England experience New Hampshire, once again refusing to be subtle. I was fully expecting the big bear to open a book and start story time Just a completely reasonable amount of autumn gorgeousness
Mount Washington: Blue Sky Jackpot
The next morning we headed for the Mount Washington Cog Railway, where the mountain famous for some of the world’s most spectacularly terrible weather decided to give us one of the nicest days imaginable.
At the summit, the landscape changed completely. The top of the mountain was rocky, exposed, and almost lunar-looking in places, with bright blue sky above us and a thick layer of cloud sitting below. It created this strange, almost upside-down perspective where we were standing in sunshine while much of the surrounding landscape disappeared beneath the clouds.
The Cog has been making the climb since 1869, using a geared rack-and-cog system to tackle the mountain’s steep grades all the way to the 6,288-foot summit. The railway’s own site even has a name for the view we got: an “undercast,” when neighboring peaks rise above a blanket of low clouds. That was exactly what it looked like from the top, and it made the whole place feel slightly unreal.
They say that on a clear day you can see five states from the summit. I have no idea whether we managed all five, but the view was spectacular either way...
The Cog Railway was part transportation, part engineering lesson, climbing Mount Washington on an extraordinarily steep track with the locomotive pushing the passenger car uphill.
On the way back down, we stopped on a grade of more than 20 degrees to wait for another train coming up. The car was getting warmer, half of us were slowly nodding off, and Scott, our very enthusiastic brakeman, was determined that this was the perfect time for questions.
Lots of questions. Bueller? Bueller? Scott remained fully committed, but the rest of us were fading fast.
Eventually, we made it back to level ground, slightly overheated, but very impressed. Mount Washington had absolutely delivered.
By the time we made it back to the coach, we were all ready for a quiet ride and maybe a nap.
Kim had other plans.
Cue John Denver.
TRAVEL TIP 3: DRESS FOR THE PLOT TWIST
Weather does not care about your itinerary. Pack the waterproof shoes, bring the umbrella, carry a raincoat, and dress in layers. We got incredibly lucky with the blue skies on Mount Washington, but the same trip also brought a nor'easter and plenty of rain. You can't control, the forecast. You can make it considerably less annoying.
Subtle, understated, very serious mountain transport The Cog’s earlier generations. Still a lot of wheels. Considerably less pink Cog Railway confidence The Cog Railway, disappearing straight into peak foliage like it planned the whole thing Above the clouds “I’m barely keeping it together. Please don’t climb me.” Same, buddy. Same. Blue skies above, clouds below. Completely surreal. Summit reached. Ghost sweatshirt still thriving
Mount Mansfield: My Personal Happy Place
Mount Mansfield in Stowe was basically my candy store.
Fall is my favorite season, and I was like a little kid from the second we got into the gondola. Surrounded by glass, we climbed through this explosion of red, gold, orange, and green, with the mountains opening up around us as we went. I could have happily ridden that gondola back and forth all day.
Then we reached the top, and somehow it got even better.
The views stretched out in every direction, the colors were ridiculously vibrant, and I kept finding another reason to stop and stare. After days of incredible scenery, this was the place that hit me hardest. It wasn’t just pretty. It was stunning.
I also happened to be wearing my new favorite dress, which felt extremely appropriate for having a full autumnal joygasm in the Green Mountains.
I love fall most of all!
Vermont: Cider, Soundtracks, & "Barbarian" Food
The day started at Cold Hollow Cider Mill, which immediately set the tone with cider, cider donuts, and hard cider. Vermont was doing very well so far.
It was also the day Kim fully embraced her role as musical director. Willie Nelson’s On the Road Again started almost as soon as we boarded the coach, followed later by the promise of Sound of Music songs on the way to Trapp Family Lodge.
She delivered. There was music. There was singing. There was no escape from the aux cord.
We headed to Trapp Family Lodge for lunch, and I was surprised to learn how much of the family’s story continued in Vermont. I hadn’t realized the Trapps had actually settled in the U.S., so seeing family photos and even the family cemetery on the property was genuinely fascinating. It made the whole place feel much more personal than I expected.
They also put on a very nice lunch for us. Bavarian-style. Not barbarian, for those who were, um, confused...
After lunch came a quick stop at Cabot Creamery and the neighboring distillery and chocolate shop. Horseradish cheese and I are not meant to be, but the maple cream liqueur more than made up for it.
By the time we boarded the Spirit of Ethan Allen III for the Lake Champlain cruise, the day had already included cider donuts, a gondola, peak foliage, musical theater, family history, Bavarian-not-barbarian lunch, cheese, chocolate, and booze.
Vermont had officially become an overachiever.
Legendary cider donuts and real live Vermonters. Sold. The Trapp Family Lodge, looking suspiciously like it was designed specifically for an autumn travel The real von Trapps, long after the credits rolled. The Trapp Family Lodge, leaning all the way into the Alpine charm. Next up: the Spirit of Ethan Allen III, ready to take us out on Lake Champlain. Lake Champlain, doing its best impression of an inland sea. Burlington waterfront, looking suspiciously well-behaved. Lake Champlain, with bonus dramatic rock formation.
Burlington: Scenic, Relaxed, & Slightly Peculiar
Burlington itself was easy to like. The waterfront was pretty, the downtown felt lively without being overwhelming, and the University of Vermont casually reminded us it had been founded in 1791. By this point in the trip, I had fully accepted that New England was going to keep throwing absurdly old American things at me.
We spent two nights there, which gave us a little more time to settle in. Dinner the first night was at The Farmhouse, which was perfectly solid. The second night, we went to Vermont Pub & Brewery, the state’s first brewpub and longest-running brewery, where we shared fish and chips and toad in the hole. My increasingly British-adjacent self felt right at home.
Dinner was followed by Ben & Jerry’s, because if you are in Vermont and there is ice cream nearby, there are certain responsibilities you simply have to accept.
Burlington also had a delightfully odd streak. Wandering around town turned up a giant bleached tree-root sculpture suspended over the sidewalk, a very homemade-looking Champ lurking outside a souvenir shop, and Zoltar waiting to dispense questionable wisdom.
Kim may have called Montpelier “Montpeculiar,” but Burlington was quietly making a case of its own.
And then Burlington gave us one final mystery.
As I was repacking at the hotel, I spotted something under the bed and reached down to retrieve it.
A quart-sized bag of Cheerios.
This would have been less strange if Mom did not, in fact, travel with a quart-sized bag of dry Cheerios of her own.
Naturally, we called her room to check.
She still had hers.
So Burlington apparently contained two unrelated travelers with quart-sized bags of dry Cheerios.
The odds seem unreasonable.
Champ, looking a little less mysterious in souvenir-shop lighting.
A Train, A Gorge, and An Unscheduled Water Feature
Our last full day on the road started with the Amtrak Vermonter from Essex Junction to White River Junction, adding one more square to the trip’s increasingly full transportation bingo card.
From there, we made a quick stop at Quechee Gorge before the itinerary took a slight detour. Woodstock had been dropped from the schedule at the last minute, so instead we crossed back into New Hampshire and stopped for lunch in West Lebanon.
We ate at 99 Restaurant & Pub with Lorraine and her son Brendon, who had already become two of our favorite travel companions on the trip. There were a lot of genuinely nice people in our group, which makes a huge difference when you’re spending this much time together. Lorraine and Brendon were especially fun to be around, and I look forward to staying in touch.
Not exactly something Great Rail Journeys can put on the itinerary, but definitely one of the better parts of the trip.
The coach, however, had one more contribution to the mayhem.
Ang and I had been taking turns using one of the few open seats, and that morning I discovered that the window seat beside the accessible door leaked. A lot. Thankfully, I looked down before sitting directly in a puddle.
When we mentioned it, the response was essentially: “Oh yeah, we know. Just don’t sit in that one.”
Cool. Excellent system.
Luckily, by the time we made it back to Boston, the day’s rain had let up. We squeezed in a little last-minute souvenir shopping before heading back to the Revere for a good night’s sleep before everyone started making their way home the next day.
The Vermonter at White River Junction: BINGO Quechee Gorge, looking appropriately dramatic in the rain A burst of fall color clinging to Quechee Gorge Boston does dramatic architecture very well Edgar Allan Poe, striding through Boston with a raven and zero interest in subtlety. Boston street art with a little teamwork and a lot of nerve
TRAVEL TIP 4: CHECK THE PACE
Escorted tours can range from very leisurely to incredibly active. Before booking, read the itinerary closely and check the notes on walking, stairs, terrain, and activity level so you know what kind of trip you're actually signing up for.
Boston Bookend
Our last morning together started early with coffee and one more walk through Boston Common and the Public Garden before Mom and Ang had to head to the airport.
The city was especially pretty that morning. The light was good, the parks were calm, and the Make Way for Ducklings statues had been dressed for a race happening that day. We also encountered one very confident squirrel who apparently took one look at Angie and decided she was obviously carrying snacks for him.
After Mom and Ang left, I still had most of the day before my evening flight, so I kept wandering. I spent more time around the Common, walked through Beacon Hill, and stopped at Granary Burying Ground, where some of the names from the earliest chapters of American history suddenly felt a lot less abstract.
By late afternoon, I finally headed for Logan. After a week of trains, coaches, boats, gondolas, weather drama, a leaking seat, and an absolutely glorious amount of fall foliage, the ride to the airport was almost suspiciously uneventful.
No traffic disaster. No security drama. No final transportation plot twist.
I’ll take it.
A final shoutout goes to the team at the Revere Hotel, who took great care of us at both ends of the trip and went out of their way to make our stays easy and comfortable. It was a great place to begin and end the adventure.
Then it was time for the red-eye home, with a camera roll full of leaves and a thoroughly completed transportation bingo card.
The actual leaves and rocks, however, stayed behind for others to enjoy.
No baggie needed.
Boston gave us one last ridiculously pretty morning. Angie made a new friend. The squirrel was confident snacks were involved. Boston Public Garden making a very strong case for one last lap The ducklings were race-ready. I was still caffeinating. Where everybody knows your name Beacon Hill was fully committed to spooky season. Paul Revere, still getting visitors more than 200 years later Boston history, casually packed into one cemetery. Park Street Church, photobombed by modern Boston The Declaration of Independence, cast in bronze because Boston does not do history halfway. Granary Burying Ground: where Boston’s history stops feeling theoretical. George Washington, keeping watch over the Public Garden Snake oil, miracle hair grow, and a very confident squirrel salesman. Sure, why not.
TRAVEL TIP 5: DOUBLE-CHECK THE PACKING LIST
A quick gear check can save you from spending a week "enjoying" your 10-year-old's bubblegum sparkle toothpaste twice a day or discovering that the watch charger you packed does not, in fact, charge your watch.
New England By The Numbers
🗓️ 6 days
🇺🇸 3 states
🚂 6 modes of transportation
💬 ~300 Kancamagus Highway mentions
🤨 2 baggies of Cheerios
🐿️ 1 squirrel who chose Angie
🍁 countless leaves admired
❤️ 3 happy Peters women
Total Mayhem Rating
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