When I’m exploring a resort, I like to anticipate what I call my “aha!’ moment, that view or run or experience of some kind that just defines not just the place, but the day. On a recent visit to Pleasant Mountain in Maine, I realized that aha moment is the same for all.
But let me start at the beginning. In the winter of 1938, a group of students, Civilian Conservation Corps members and other volunteers set out to create the perfect trail to feed their passion for skiing.
They worked all summer and fall clearing just the right line down one of Bridgton, Maine’s most impressive peaks: Pleasant Mountain.
That winter they skied it every day they could. Word got out. Three years later a rope tow was installed, and by 1957, a chairlift took skiers from far and near up high to experience the beauty those original skiers sought. Pleasant Mountain earned its stripes.
Fast forward to winter 2026. I’ve arrived at Pleasant Mountain midday on a crisp, sunny day, The base lodge is bustling and the lifts are spinning. Under bluebird skies on a perfect winter day, I understood completely why those skiers worked so hard to access this peak way back when.
From the lovely greens to the steeper blues and blacks, Pleasant Mountain delivers. Pleasant isn’t a show-offy or braggy mountain; that’s why you may not know that from its peak – and I say this as a lucky skier who’s been just about everywhere – you’ll soak in one of the most breathtaking mountain views in the region.
With shiny Mount Washington as a centerpiece and the Presidential Range sprawling out around it, you’ll be awestruck. No hyperbole there.
Pleasant is truly a mountain for everyone. There’s a super mellow magic carpet where learners are gaining their stripes. To the right of that are some longer learning trails, spots where you can warm up well or – if a learner – experience the feel of getting up on the mountain in a totally skiable way.
Across the front face of the mountain you’ll find a trail network that may look unassuming on a trail map, but that skis so very fun. Just steep enough groomers have side trails that are narrow and winding; thick with trees on each side. You can bob and weave to your heart’s delight, and use the same lift all you want while making each run feel new.
Pleasant might be known to you by a different name.
In 1988, it was sold to the Shawnee Mountain Company and, as its website says with a bit of a wink, “in a burst of brand synergy, was renamed ‘Shawnee Peak’ to create a connection” between the Maine mountain and the Pennsylvania company. A name isn’t everything, course, and the mountain continued to attract ski loyalists and multi-generational ski families. They continued building up their snowmaking (which debuted after the miserable snowless winter of 1977).
In 2022, Shawnee was purchased by Boyne Resorts. Anyone worried about corporate takeover was put at ease from day one. Boyne’s first act was to reclaim the name “Pleasant Mountain,” proof they were dedicated not just to preserving but pumping up that brand born in 1938.
They’ve delivered with investments like The Summit Express, the resort’s first high-speed quad that now makes lapping a ton of vertical a snap, and by improving the mountain across the board.
This day, I can see it’s working. I arrive midday and while it’s not super crowded, it’s busy. And yet, every trail I ski is well-covered and a delight to ski. My friends and I carve along with confidence, taking in the views and loving our speedy runs between.
Even the lift rides up are fun. From the Pine Quad, we watch free skiers and snowboarders taking on the features at the resort’s impressive park. From the Summit Express we have a front row view of a giant salmon race going on that day. With the Olympics on every screen in the lodge and at folk’s homes, we found our own live racing experience.
The back side of Pleasant offers more steeps and challenge, too. But my favorite run is one that’s all about the timing – and that aha moment: Since Pleasant is open for night skiing, you can ski right through the sunset there.
We head over to the aptly-named Sunset Boulevard, a cruiser that winds you around to first see the sun sinking behind the mountains and then, after a turn, the magnificent alpenglow across Mount Washington itself. It’s so captivating, we lap it three times. I am drawn to it like a force of nature. It reminds me of sunsets in Costa Rica, where everyone stops to soak it in each evening. I can tell you with all sincerity that this run is a core memory ski experience.
There’s more, too. As night falls, the resort transitions to a teen hangout. They’re loud and happy and yes, they kind of take over the place. As I ski below the lights and around them, rather than think “get off my lawn,” I celebrate a place where kids are active, outdoors, social and best of all, barely looking at their screens. Full approval here.
The pub is great with live music and even a beer brewed just for them. We dine and relax as the teens ski on outside. It had been decades since I’d skied Pleasant. It’s back on my regular rotation. Put it on yours as well.
Pleasant Mountain an avalanche of fun
Where: Pleasant Mountain is located in Bridgton, Maine, about two and a half hours from Boston and about a half hour from North Conway proper. Parking there is plentiful, and hours run from 8:30 a.m. to 8 p.m. daily, extending to 9 p.m. every Monday for their “Monday Madness.”
What: Pleasant features 44 well maintained trails with top to bottom choices for every level. You’ll find a magic carpet as well as six chairlifts, a decent-sized base lodge with rentals, a ski shop and more.
There are ski school lessons for every level including their “Small Fry Try” program for children ages 2-3, a rare offering for any ski resort. Little ones go out and spend 45 minutes getting a feel for the sport. There are also weekly seasonal programs.
As always, booking tickets online ahead of time is a good choice.
Where to stay: Pleasant Mountain has lots of slope side condos that can be rented short term, as well as a few special cabins scattered in private yet accessible spots across the mountain. For a truly special stay, consider the Tuckerman’s Cabin (https://www.pleasantmountain.com/tuckermans-cabin) for a feel like it’s your own private ski resort.
The greater North Conway area is close by too, about a half hour drive that’s easy and pretty. There you can find just about any type of lodging (https://www.visitmwv.com/) there is.
Dining: The base lodge itself serves up great classic base lodge food, and upstairs you’ll find Blizzard’s Pub with a crackling fireplace, live entertainment and great food. The flatbread is on point, and the reuben wowed this reuben connoisseur. You can also find tons of dining in North Conway.
Extra fun: The resort’s event calendar is full of fun choices, like their slope side pancake breakfast on National Pancake day (Feb. 28). You’ll also find live music, Monday Madness and other fun extras like the annual mattress race day and Spring Fling.
