Vermont is a skier’s delight. With storybook villages, luxury ski lodges, and world-class terrain, the Green Mountain State has long been the East Coast’s answer to the Alps.
Home to more than 20 ski areas, there’s a mountain for every style of skier, from beginners to expert-level professionals. Perfectly groomed slopes and top-tier snowmaking technology attract passionate skiers to this winter playground from the first snowfall in November until the season winds down in April. Private charter flights to Vermont are easy thanks to Tradewind Aviation, where getting there with confidence is not just convenient—it’s part of the experience.
Fly Personal with Tradewind
The best ski trips often begin long before you reach the mountain. Skip the stress of commercial air travel and long drives to the airport by booking a private charter flight with Tradewind that works with your schedule. Tradewind Aviation flights depart from private FBO terminals, avoiding crowds of commercial airports, TSA and security delays, and allowing guests to arrive just 30 minutes prior to departure. Their fleet of Pilatus PC-12 aircraft can land on shorter, harder-to-reach runways, getting guests closer to their final destination and cutting out unnecessary ground transportation. With direct access to airports in Bennington, Rutland, Springfield, and Stowe, Tradewind offers a gateway to exceptional skiing at Vermont ski resorts.
From the moment your gear is loaded onto the aircraft with care, your alpine escape begins. Settle into comfortable leather seating with friends, family, and even your four-legged companion, and enjoy a flight that feels like a private retreat. Sip champagne, take in views of snow-covered peaks, and touch down relaxed and ready to hit the slopes. From East Coast hubs like Boston, Westchester, Teterboro, Morristown, and Farmingdale, flight times are typically an hour or less
With a Tradewind private charter, there’s no need to miss out on an epic ski weekend. Here are a few easily accessible destinations with the best skiing in Vermont.
Killington, The Beast of the East
Located in southern Vermont, Killington reigns as the largest ski resort in the eastern United States. Nicknamed “The Beast of the East” for its sheer scale, Killington spans more than 1,500 acres of skiable terrain with over 200 trails and 22 lifts across seven interconnected peaks: Killington Peak, Skye Peak, Bear Mountain, Snowden, Ramshead, Ridge, and Norcross. The resort boasts the highest vertical drop in New England and Vermont’s second-highest summit at 4,241 feet. All said, it’s one of the best places to ski in Vermont. Here, beginners can learn to carve their first turns while advanced skiers can conquer the steepest trails across multiple peaks, day after day.
With one of the most advanced snowmaking systems in the country, Killington is typically the first mountain in Vermont to open each season (usually November), and the last to close, extending its spring skiing well into May. At day’s end, the Killington Grand Resort Hotel, the mountain’s only full-service property, offers ski-bridge access, a heated pool, and mountain views
The adventure doesn’t end when the lifts stop, as Killington is also famous for its nightlife. The après-ski-to-pub crawl is a local ritual beginning with craft beers and regional cocktails at lively base lodges, and continuing into town, where more than 100 restaurants and bars with live music and dancing keep the mountain spirit alive.
Just ten minutes away lies Pico Mountain, Killington’s smaller, quieter sister resort. With 58 trails and a laid-back atmosphere, Pico offers a more intimate experience that’s well-suited to family skiing in Vermont.
How to get there: Book a Tradewind private charter flight into Rutland Southern Vermont Regional (RUT/KRUT).
Stowe & Sugarbush: Northern Vermont’s Refined Retreats
In northern Vermont, the town of Stowe sits at the base of Mount Mansfield, the state’s highest peak. This storybook mountain village embodies classic New England charm: a soaring white church steeple, covered bridges, and Main Street lined with boutiques, art galleries, and cozy cafés. A Stowe flight with Tradewind Aviation delivers you just 15 minutes from the slopes at Stowe Mountain Resort, and a scenic 30-minute drive from Sugarbush, making both easily accessible for a weekend on the slopes.
Skiing at Stowe Mountain Resort is as exhilarating as it is beautiful. On one side, Spruce Peak offers broad runs ideal for beginners and families; on the other, connected by a high-speed gondola, Mount Mansfield tempts experts with its steep, ungroomed “Front Four” – Goat, Starr, National, and Liftline. These double black diamond trails have defined the challenging East Coast skiing experience for generations.
After the day’s final run, toast the evening with champagne and seafood towers at The Tipsy Trout, located within The Lodge at Spruce Peak, or settle into Cork Wine Bar for an intimate farm-to-fork dinner and a glass of organic wine.
Stay slope-side at The Lodge at Spruce Peak, Stowe’s only ski-in/ski-out resort, and rejuvenate in the spa and heated outdoor pool. Couples seeking more seclusion can retreat to the von Trapp Family Lodge, an alpine-inspired estate offering cross-country trails, wood-burning fireplaces, and old-world romance. Another option just minutes from the village is Edson Hill, a luxury inn and restaurant set on 38 private acres.
A short, scenic drive south leads to Sugarbush Resort in the Mad River Valley, a less-crowded alternative with stunning natural beauty. The atmosphere is relaxed, the kind of place where couples and small groups come for the skiing and stay for the serene surroundings. The resort’s two mountains, Lincoln Peak and Mount Ellen, offer 2,600 feet of vertical terrain and 111 trails. There are many options for places to stay close to the resort. The Pitcher Inn, a Relais & Châteaux property in the village of Warren, features an acclaimed farm-to-table restaurant and wine cellar.
How to get there: Book a Tradewind private charter to Morrisville-Stowe Airport (MVL/KMVL).
Southern Vermont’s Ski Triangle: Stratton, Mount Snow & Bromley
For skiers arriving by Tradewind private charter, Bennington serves as the gateway to Southern Vermont’s classic ski triangle—Stratton, Mount Snow, and Bromley—all within a 45-minute drive of touchdown. Each mountain offers its own distinctive style and atmosphere, making this region ideal for those who want variety.
Stratton Mountain Resort has an alpine-style base village with shops, boutiques, gear shops, bars, restaurants, and places to stay. In addition to skiing, it also hosts music festivals, crafts fairs, and culinary events that draw an affluent crowd from New York and Boston, so weekends can get busy. The ski mountain has 99 trails, glades, and five terrain parks, and it’s excellent for beginner and intermediate skiers.
A short drive west, Mount Snow offers a more family-friendly dynamic with approachable terrain, excellent snowmaking, and a welcoming base village. Parents can ski while children hone their skills in ski school. When the day winds down, gather for dinner at The Hermitage Inn, a Relais & Châteaux property with a spectacular food and wine program.
Rounding out the trio of Southern Vermont skiing is Bromley Mountain, nicknamed “Sun Mountain” for its sunny, south-facing slopes. Small and unpretentious, Bromley is perfect for families seeking a relaxed getaway or couples in search of quiet charm. The slopes here are evenly split between beginner, intermediate, and advanced. Stay nearby in Manchester Village at The Reluctant Panther Inn, a boutique luxury hotel with fine dining.
How to get there: Book a Tradewind private charter into William H. Morse State Airport (DDH/KDDH) in Bennington.
Central Vermont: Okemo & Magic Mountain
Central Vermont offers two distinctly different skiing experiences.
Okemo Mountain Resort is polished and family-friendly with 123 trails that seem more gentle than extreme. About one-third are wide runs for beginners; one-third caters to intermediate skiers with classic fall-line descents; and the remaining third deliver thrilling glades and steeper pitches for experts.
Okemo’s annual New Year’s Eve fireworks and DJ party runs early in the evening (5–8 p.m.), which allows skiers to ring in the new year without missing first tracks the next morning. For accommodations, stay in the village at Jackson Gore Inn, where fireplaces and outdoor hot tubs overlook the lifts. Couples may prefer the romantic Castle Hill Resort & Spa, an Edwardian-style mansion and member of Historic Hotels of America. Dining in nearby Ludlow is a treat: The Downtown Grocery, a cozy fine-dining spot with just a handful of tables, serves inventive, farm-to-table dishes (reservations essential), while Homestyle Restaurant blends local craft culture with comfort food.
By contrast, Magic Mountain in Londonderry is Vermont’s throwback, a resort that trades glitz for character. There are no high-speed lifts here, just deep snow, steep wooded trails, and a sense of camaraderie that harkens back to skiing’s golden age. It’s a mountain for purists. Join the locals for a craft brew and live music at the Black Line Tavern, the mountain’s lively après hub. Stay nearby at The Grafton Inn, a historic property dating back to 1801, where creaky floors, candlelit dinners, and colonial charm make for a quintessential Vermont retreat.
How to get there: Book a Tradewind private charter flight into Hartness State Airport (VSF/KVSF) in Springfield.
From the southern peaks of Killington to the northern slopes of Stowe, Tradewind Aviation connects you to Vermont’s finest ski resorts in effortless style with flexible scheduling, attentive service, and the quiet luxury of your own aircraft. As winter approaches and the first snow begins to fall, there’s no better time to plan your Vermont ski escape.
To learn more about Tradewind’s private charter flights to Vermont and booking your vacation, please visit our website. To receive a private charter quote, please submit an inquiry here or contact our specialists at sales@flytradewind.com or 1-800-376-7922 option 2.