Sugarloaf
Five years in.
The mountain finally matches the legend.
Mt. Snow. Stowe. Okemo. Sunday River. Four years, four destinations, one ever-growing crew of skiers and riders who keep coming back. Every January, the same Friday-through-Monday rhythm. Every January, the bar gets pushed a little higher.
For Year 5, we are pointed at the place we've been circling all along — Sugarloaf, Maine. Second-longest vertical in New England. The highest summit in the region. The only lift-served above-treeline skiing east of the Rockies. Real wilderness, real mountain, real weather. Three nights in a luxury Airbnb tucked just below the resort, with the hot tub steaming under a sky absolutely cluttered with stars.
You show up, you ski hard, you eat impossibly well, you sleep deeply. Everything else — lodging, groceries, every meal Friday dinner through Monday breakfast, all the logistics — is handled. Your only jobs are getting here, buying your lift ticket, and being ready for first chair.
Maine's giant.
Sugarloaf isn't a polished resort experience pretending to be a mountain. It's a mountain that happens to have lifts. Numbers tell some of the story.
Second-longest continuous vertical in New England — top to base, no breaks.
The highest peak elevation of any ski resort in New England.
Greens to double blacks, plus thirty named glades and six terrain parks.
Including Brackett Basin sidecountry — cliffs, chutes, glades, room to roam.
Fifteen lifts moving twenty-five thousand skiers an hour. Spread across three faces. On a clear day from the summit you can see Mount Washington, the Bigelow Range, and on a really clear day, Canada.
Two pieces of terrain you cannot ski anywhere else in the East.
Above the trees.
The white cap on the resort's logo isn't decorative. It's the Snowfields — the only lift-served above-treeline skiing on the East Coast. Open-bowl alpine terrain, 360-degree views, and the kind of wide, white emptiness skiers from the West think doesn't exist out here.
The front face — White Nitro, Powder Keg, Bubblecuffer, Gondi Line — comes off the lift. The backside is a short hike to the 4,249-foot peak. Hit it on a bluebird day after a fresh dump and there is nowhere on earth you'd rather be.
The wild side.
On the other side of the resort, Brackett Basin is a sprawl of cliffs, chutes, and gladed terrain that turned Sugarloaf into a real expert mountain. Ski it all day and never repeat a line. The outer reaches — Birler, Edger, Sweeper glades — are where the locals disappear when the front side gets tracked out.
It's the antidote to manicured corduroy. Trees, drops, pillows, surprises. If your crew has skiers ready to push it, Brackett is the reward.
A house designed
for this exact group.
A premium Airbnb selected for the trip — minutes from the mountain access road, with the layout and amenities a crew of twelve-to-fifteen actually needs after a long day in the cold.
A kitchen built for serious cooking. Generous counter space, real range, and the room a chef needs to plate fifteen dinners without anyone bumping elbows. Multiple living areas so the late-night card game and the early-bed crew each get what they need. A hot tub for slow recovery after a hard day on the mountain.
Specific address and check-in details will go out one week before the trip. For now, just trust the program — every year so far the house has been the quiet highlight.
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Hot tubSlow recovery for legs that earned it. The single most-used feature every year, regardless of weather.
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Chef's kitchenGenerous counter space, real range, the room and equipment to cook restaurant-quality meals for the full group.
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Multiple living areasRoom enough that the late-night card game and the 9 PM bed crew never have to negotiate the same couch.
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Sleeping for the full crewBeds for the whole 12-to-15 person group — proper mattresses, considered configurations, no air mattresses on a floor.
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Minutes from the mountainSited just off the Sugarloaf access road. No long morning commute, no fuss getting there for first chair.
Three full dinners.
Every plate, restaurant quality.
Austin runs the kitchen all weekend — premium ingredients, gluten-free friendly across the board, and three full dinners designed fresh each year. Exact menus stay under wraps until the welcome letter hits your pillow, but the standard is the same one that's held every year: restaurant-quality on every plate, served at a long table with the right pour in your glass.
What Saturday
actually looks like.
The trip runs on a quiet schedule — built across four years of trial and error, designed to maximize mountain time and dinner time without burning anyone out.
The Bag.
The Widowmaker.
The valley.
Sugarloaf's après scene is one of the best in the East — not polished, not packaged, just genuinely lived-in. If you want to stretch the day with a beer on the way back to the house, a few spots are worth knowing. Entirely your call — the group plan ends at last chair, and the house will be ready whenever you roll in.
The Bag & Kettle
The legendary Bag Burger with top-secret Bag sauce, house-brewed beer, and the same faces at the bar for thirty-five years. The original Loaf après-ski.
The Widowmaker Lounge
Two stories above the base lodge. Twenty beers on tap, panoramic mountain views from the high-tops, and live music most nights. Hard to find a stool at après hour.
The Rack BBQ
The real ski bar at Sugarloaf. BBQ, beer, locals. Lower-key than the Widowmaker, exactly where you want to land on a Saturday after a long day.
Plan your route.
Carrabassett Valley is far north — that's part of the appeal. Real wilderness means real driving. Numbers below are estimates; pad your departure on Friday for snow and weather.
Lift tickets.
Lift tickets aren't included — you book your own days. MLK Weekend is Sugarloaf's peak holiday window, so the window walk-up rate is steep. Buy online in advance and you'll save meaningfully. Sugarloaf's 3-Day Ticket Pack is usually the move for the trip.
Final 2026/27 pricing posts to sugarloaf.com in the fall — these estimates are based on recent seasons and will get firmed up in the one-week-out update.
If you have an Ikon Pass.
Sugarloaf is on the Ikon — both tiers. Ikon Base gives you 5 days at Sugarloaf with no holiday blackouts at this resort. Full Ikon gives you 7 days. If you've already got the pass, your lift ticket is sorted.
Five years of this.
From the cruisers of southern Vermont to the only above-treeline lift-served terrain in the East. Each year a step bigger.
All-inclusive, almost.
What's included
- Three nights in a premium Airbnb (Fri–Mon)
- Friday welcome dinner + apps & drinks
- Three full breakfasts (Sat / Sun / Mon)
- Two make-your-own sandwich lunches
- Nightly après-ski apps spread
- Three restaurant-quality dinners (Fri / Sat / Sun)
- Cocktails, wine, and bar to match
- All groceries, all cooking, all cleanup
- Austin's coordination from arrival to checkout
What you handle
- Your lift ticket (1–3 days, your call)
- Skis, snowboard, boots, gear
- Getting yourself to the house
- Any extra personal beverages or snacks
- Spending money for the Bag Burger run
Twelve to fifteen seats.
They go fast.
Returning crew gets first dibs through early summer. After that, the trip opens to anyone who's been on the wait-and-see list.
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Early Bird Through June 12$700 / person $250 deposit
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Regular June 13 – 26$750 / person $300 deposit
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Late After June 26$800 / person $350 deposit
You're in.
Last step — send $250 deposit (1 spot) via Venmo and your spot is officially locked. Scan the QR with your phone, or tap the button if you're already on mobile.