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Vermont’s Oldest Ski Town Bars

Vermont's Oldest Ski Town Bars

Vermonters tend to like their bars the way they like their mountains- unpretentious, untamed, and covered in snow. The laid-back and community-minded nature of Vermonters lends itself to some truly remarkable apres-ski bars. Among them are a few midcentury staples that have stood the test of time and weathered the changing need of the local ski community.

Vermont established itself as a ski destination as early as 1934 when Stowe Mountain Resort carved a chunk out of the south side of Mt. Mansfield. It was swiftly followed by Pico Mountain in 1934, Bromley Mountain in 1936, and Saskadena Six Ski Area (formerly known as Suicide Six) in 1937. Where resorts appear, apres-ski culture will inevitably follow. Long days of slashing powder and freezing fingers would not be half as gratifying without a frosty beer and warm fire to balance it out.

A few of the bars on this list date back to a time when tow ropes and T-bars were more prevalent than the three to four-seat speed lifts we see today. Many of them still serve the apres-ski crowd, shifting with the times to serve the best local beer and live entertainment that the Green Mountain state has to offer.

1924 Johnny Seesaws - Bromley Mountain - Peru, VT

Bromley Mountain has a reputation as a family-friendly getaway, both in the summer and winter. As home to one of the earliest ski mountains in Vermont, the town of Peru can certainly lay claim to some of the oldest ski town bars. The oldest and most beloved is Johnny Seesaws, A Peru staple that has provided food and entertainment to the Bromley apres-ski crowd since the 1920s.

Johnny Seesaws was originally a dance house, then a restaurant and lodge. The vibe is a mixture of the classic Vermont log cabin and your family’s cozy ski house. Visitors and locals alike sink into cozy nooks beneath the building’s original log beam ceiling to eat, drink and be merry. Do not miss out on the Prime Rib, a must-have staple of this old ski bar.

The outside patio caters to the apres-ski crowd where firepits and local beers keep the visiting crowd warm. Locals tend to prefer the basement bar. Higher prices for basic Vermont brews reflect the proximity to Bromley Mountain, but locals and visitors alike return for the live music and atmosphere.

1950s The Matterhorn - Stowe Resort - Stowe, VT

The Matterhorn certainly falls into the category of one of the oldest ski town bars in Vermont. It has catered to the Stowe resort apres-ski crowd since the 1950s. The Matterhorn is a reflection of the eclectic crowd that dominates Stowe in all seasons. Locals and visitors combined to create a unique atmosphere of practical sophistication. This eclectic bar prides itself not only on its food and drink but on its entertainment. The unassuming bar has hosted several famous bands over the years including the Monkees and The Grateful Dead.

Like most rural ski-town bars, the food is not the reason that skiers flock there every winter evening. The full bar, lively atmosphere, and live music provide the perfect counterpoint to a day spent on the mountain. The Matterhorn plays host to a variety of clientele from local flannel-wearing Vermonters drinking Heady Topper straight out of the can, to wealthy New Yorkers sipping cocktails in their perfectly coordinated apres-ski outfits.

1959 Wunderbar - Sugarbush - Warren, VT

The Sugarbush lodge (while not quite as old as Stowe) certainly has reason to claim its place on this list. According to the Sugarbush website, the Wunderbar is the first bar to open on a ski resort. The owners had to convince the state that the name “Wunderbar,” which means wonderful in German, did not break the state’s laws which used to prohibit the use of the word “bar” in the name of a restaurant.

The Wunderbar opened in 1959 and was instantly successful. It maintained its popularity throughout the ’60s and 70s and was THE place to be seen, especially if you were single. These days, Wunderbar has fallen out of favor and the Castlerock Pub has taken its place as the most popular bar on the mountain. Although, Wunderbar is still open on the weekends for anyone who wants a quick snack and drink before heading back out on the slopes.

Wunderbar still maintains its 70s retro style on the top floor and added a second story for the “Wunder Down Under.” The Wunderbar has lost a little of its old-time glamor as Sugarbush has morphed from a celebrity destination to family-friendly over the years. Both the Wunderbar and Castlerock Pub are casual to the point of silliness. Children stream in and around the tables, adults remove ski boots to rest cold feet by the fire, and local brews are downed quickly and with pleasure.

wunderbar at sugarbush ski resort vermont

1960 The Pickle Barrel & 1963 The Wobbly Barn - Killington & Pico Resorts - Killington, VT

The Town of Killington is home to two ski resorts, Killington and Pico, and two competing old ski-town bars, the Pickle Barrel and Wobbly Barn. You would never expect a small town in middle-of-nowhere Vermont to have several nightlife offerings, but these old ski town bars have made a name for themselves for both their hospitality and entertainment.

Vermont’s rural status makes it the perfect place to catch live bands, whether they are just starting out or popular and well-known. Both the Wobbly Barn and the Pickle Barrel have been around since the early 1960s. Every day during ski season these steakhouse-style restaurants transform from family-friendly restaurants to late-night college parties within a few hours.

The Pickle Barrel has a rich history. In the 1960s, it went from a dance hall to a bar/movie theater. Today, the Pickle Barrel has reached its ultimate transformation as a restaurant/nightclub. Like many restaurants in Vermont, it serves a classic selection of steaks, salads, and sides. A $20 cover charge usually gets you access to live music. Over the years, the Pickle Barrel has hosted several big names in the music industry including Snoop Dogg, the Whalers, the Roots, Wu-Tang, and Warren Zevon.

The Wobbly Barn menu changes seasonally but features a similar array of steaks and sides. Unlike the Pickle Barrel, if you eat at the Wobbly Barn admittance to the nightclub is complimentary. This barn was built from the pieces of several old New England barns, but do not take the “wobbly” in the name too seriously. This bar has stood the test of thousands of dancing feet since 1963 and continues to be a staple of Killington apres-ski culture.

1960 Red Fox Inn - Stratton, Bromley, Magic Mountain - Bondville, VT

The Red Fox Inn is the place to be in the tiny town of Bondville, especially during ski season. The inn is built into a repurposed farmhouse located within 10 miles of Stratton, Bromley, and Magic Mountain. With two separate food menus, the Red Fox inn has a little something for everyone. The top floor serves hearty foods to fill you up for the next day’s riding and the downstairs has comfort food with plenty of Irish food specials.

A welcome relief from the tourist-centric ski mountains, the “Fox” offers classic Vermont hospitality and live music every night during the season. The Logans, a husband and wife team that runs the inn these days, purchased the inn in 1984 after working for years as bartenders and waitstaff. Visit for the infamous St. Paddy’s Day parade run by the Logans and visit the inn afterward for classic Irish fare, Guinness, and plenty of Jameson. For a tourist hotspot, the Fox certainly offers a glimpse into what it’s like to live in Vermont year-round. Family-owned businesses that are essential to the community, classic Vermont fare, and cozy winter evenings listening to music with close friends and family.

While they are not necessarily known for the food, Vermont’s oldest ski town bars offer a welcoming atmosphere that will warm you from fingers to toes. These bars are made great not by the variety of beers or sold-out local bands, but by the memories that cause visitors to return year after year. Check them out the next time you hit the slopes for an unforgettable Vermont experience.

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