During the winter months our Green Mountains are a mecca for snow-related activities; let us point you in the right direction. For skiing and riding, Killington and Pico Ski Resorts are right on our doorstep. Our region also offers ample opportunities for Nordic skiing, snowshoeing, riding a Fat Bike, sledding, tubing, ice skating, ice climbing and even a sleigh ride.
If you can walk, you can snowshoe! Rent a pair from our front desk to take an evening stroll on the adjoining Golf Course. You’ll be amazed by the moon-lit illuminated, clear Vermont skies! Want to hike something more challenging? Try the Green Mountain Trails in Pittsfield and make your way up to Shrek’s Cabin!
Ride a Ski Bike
Looking for a new wat to conquer the slopes? Check our ski biking! Combine the exhilaration of Skiing, the flow of Snowboarding and control of Mountain Biking, and you have one of the fastest growing winter sports in the nation - Ski Biking!
Sledding & Tubing
We have a fantastic sledding hill on our property. You are encouraged to borrow a sled from us and give it a try! You can also check out Killington’s Tubing Park which offers a lighted, multi-lane, lift-serviced good time for all ages.
Check out The Foundry’s Skating Rink on the pond!
Our good friends at Vermont Adventure Tours offer first-timer to advance ice climbing tours in the area. Want to climb and stay warm? They also have 2 indoor rock climbing gym locations.
Billings Farm & Museum in Woodstock offers horse-drawn sleigh rides during the winter. Check their website for more information.
Head out from our parking lot on Green Mountain National Golf Course or try out the trails at Mountain Meadows or Mountain Top.
Photos Trailside Inn
Killington Ski Resort
The Beast of the East, is the largest and most diverse ski resort on the East Coast. It has it all, wide groomers, narrow steeps, moguls, terrain parks and glades. Over 3,000 skiable acres in fact, with 155 trails serviced by 22 lifts including 2 high-speed gondolas. With 3,050 feet of vertical drop, Killington continually takes the title of the first resort to open and the last to close with annual snowfalls of 21 feet and over 80% snowmaking coverage. Like hanging out in the terrain park? Killington has great progression in their 6 parks, including their 500-foot long Superpipe with 18 foot walls. The Burton Stash is an all-natural terrain park with 50+ features both on trail and in the woods. The Stash is the only terrain park in the east that gets even better on powder days. All Killington lift tickets include access to Pico Ski Resort as well.
Pico Ski Resort
Pico is a favorite ski destination among locals and visiting families. Pico has gentle learning smooth cruisers, classic narrow New England steeps and fantastic glades on 52 trails and a terrain park serviced by 7 lifts. Pico’s vertical drop is just shy of 2,000 feet – taller than 80% of Vermont ski areas. Families love Pico for its smaller crowds and single base lodge allowing kids some freedom to explore on their own. It’s big Vermont skiing at a great, family-friendly price.
We love and cater to our season pass holders and multiple visit guests by offering preseason sales. Want to know more? Give us a call at (802) 422-8800 for details. Last season our guests received discounts up to 25% during our sale.
Photos Trailside Inn
Need Lift Tickets?
We offer a limited supply of lift tickets for Killington and Pico every winter. You can purchase your tickets online after selecting your room type from our website. You can also call us for pricing and availability.
Think you got what it takes to ski like a local and go backcountry?
Check out our good friends at Killington Mountain Guides. Together, we offer guide service ski packages on untouched, private land to deep National Forest tours.
Want to hit a few of Vermont’s finest ski resorts?
Why not make The Trailside Inn your basecamp for your ski and ride vacation. Besides having Killington and Pico at our doorstep, Sugarbush, Mad River Glen and Okemo Mountain are all easy day trips from our Inn.
Summer offers an exciting array of outdoor activities. For the golfers out there, it doesn’t get much more convenient, since the Trailside Inn overlooks the third fairway of Vermont’s #1-voted public golf course—the Green Mountain National Golf Course. And when you stay at our Inn you’ll also have easy access to some world-class hiking trails, including the Appalachian Trail (one mile away) and Vermont’s famed Long Trail (four miles away). And don’t forget about our mountain and road biking, river tubing, breweries, fishing, and more.
Love to Golf?
Green Mountain National Golf Course overlooks our property. We are a Stay & Play partner, giving you the best price for golf packages. You can also play at Killington Golf Course located only 6 miles away. If the weather isn’t cooperating, you can try out the simulators at Stonehedge Indoor Golf Center in Rutland.
Killington Adventure Center & Free Summer Concert Series
At the brand-new Killington Adventure Center, you can soar through the sky, hang high from a rope course, get lost in a maze or rip down the mountain coaster. Built in summer 2015, the Adventure Center is great for an afternoon of fun for couples to families. The Adventure Center has a mountain coaster, skyride, ropes course, disc golf, ATV and Segway tours, Terra Maze, gold mining and scenic gondola rides. The Adventure Center is expanding this summer with dual racing zip lines, free jump, tubing park and a few other attractions on the way.
On Saturday afternoons, check out Killington’s free outdoor concert series Cooler in the Mountains; located at the Adventure Center. Bring some lawn chairs along with your own cooler (or grab a drink from the Long Trail Pub)! There are also free outdoor concerts at Killington’s Sherburne Library on Thursday nights. It’s very family-friendly with a pick-up soccer game by the local kids usually occurring. Their calendar, along with other town events, can be found here.
Mountain Biking & Cycling
The Killington region is quickly becoming the Northeast’s mountain biking hotspot. With 3 separate major trail systems and a fourth breaking ground this spring, you have lots of options for riding.
For lift service riding, head over to Killington Resort. They are in phase 3 of 5 of a major expansion project with new trails in the Snowshed area, including wide, mellow beginner trails, intermediate options with switchbacks and banked turns and of course technical free ride terrain for the most advanced riders. The Snowshed Express Quad and K-1 Express Gondola run daily for trail access.
Located a short 4-miles from the Trailside Inn, Pittsfield’s famed Green Mountain Trails offer some fantastic riding with a thousand feet of climbing and descending. Though a majority of the trails are relatively smooth and flowy, there are several miles of rooty, rocky, technical singlet rack as well. Over 100 bermed switchbacks make the long descents a blast for mountain bikers. Most of the uphills are gradual and forgiving on the quads, but challenging uphills are also an option. Depending on your route, descents can linger for as long as six miles. The trails system is free to the public. You can support the trails by purchasing a trail map from us or the donation box at the trailhead.
About 25 minutes away, riders from beginner to advanced can flow at Pine Hill Park. Offering 16 miles of single-track spread over 325 acres, it offers the flattest trail system in the area. Trails are free for use but donations are greatly appreciated as the system is built and maintained by a dedicated group of volunteers.
The Killington Mountain Bike Club has led the charge for a new system of trails in Gifford Woods State Park, a mile from Trailside. As soon as they are open, we will let you know!
If you are in the area and need anything from service to a new bike, check out our friends at Alpine Bike Works. They also do fat bike rentals and sales.
Nothing compares to the simple pleasure of riding a bike, and nothing compares to riding your bike through the Green Mountains of Vermont. The area has everything from peaceful valley rides, mountain pass climbs and endless miles of gravel. As cyclists ourselves, we can help you plan routes to make the most of your day riding. Looking for something more formal? Check out Wrenegade Sport’s Farm to Fork Fondo (a personal favorite), the Killington Stage Race, the Long Trail Century Ride or the Vermont Overland Gravel Grind.
Local Hiking Trails
Vermont is 80% covered in forest, making its Green Mountains a hikers’ wonderland. We are located on the edge of the National Forest only a couple miles from both the Appalachian and Long Trails. The hiking terrain is very diverse from easy waterfall strolls to steep mountain scrambles. Some of our favorites are: Roaring Brook Falls (easy); Deer Leap, Stone Steps or Pico Summit (intermediate); and the Bucklin Trail to Killington summit (advanced). There are, however, many trail choices beyond the guide. We can help point you in the right direction based on what you are looking for. Please be prepared for hiking with proper footwear, water and emergency gear.
Swimming, Tubing & Paddling
It is a right of passage in Vermont to spend a lazy day floating down the river on a tube or jumping into a swimming hole. For tubing, we like Tweed River Tubing in Stockbridge (12 mins away). The best swimming holes are Peavine and Warren Falls. With a slightly longer drive, you can hit a dozen in the small town of Lincoln (pretty drive too!).
Want to spend some time on the water instead? Chittenden Reservoir, a 750-acre reservoir surrounded by Green Mountain National Forest, is a local hidden gem. Boat rentals can be found at Blue Ridge Outfitters. For large groups, we suggest using Vermont Adventure Tours for rentals. You can also try standup paddle boarding on Woodward Reservoir. First Stop will do drop-off in the parking lot for you. There are also standup paddle board Yoga classes offered there too! With a longer drive, you can also check out Silver Lake State Park in Barnard and Lake Dunmore State Park in Middlebury.
Vermont Craft Brew Tours & Day Tripping
Since life is too short to drink cheap beer, you might as well do a Vermont Beer tour! Vermont is a small state with some big beers! There are a number of great driving loops from Trailside allowing you to hit some excellent breweries – everything from tasting rooms to full restaurants. We can help you plan out a day with a bunch of Vermont roadside local charm and some of the tourist stuff as well. It is the same stuff we do!
Along the way you will get to experience Scenic Route 100, National Forest mountain passes, roadside stands and more. It is always fun to include ice cream from Ben & Jerry’s Factory, hot cider donuts from Cold Hollow Cider or a new best friend from Vermont Teddy Bear.
These are a few of our favorite breweries. Be sure to check out the Vermont Brewers Association for more info.
Don’t want to drive? We can set up a party bus for you and your friends so that the driving is done for you, give us a call (802) 422-8800!
Vermont Farmer Markets, Berry Picking, Maple Syrup & Cheese
Pick up some fresh produce and more at the Rutland Farmers Market. It is the largest one in the state. In Woodstock, there is the Mt. Tom Market and the Woodstock Farmers Market (great sandwiches too!). Have more of a sweet tooth? Pick your own berries at Sunshine Berry Farm in Rochester or try some pure maple syrup and cheese at Sugarbush Farm in Woodstock. Fresh apples and pies can be found at Mendon Orchards.
Woodstock & Quechee
Billing's Farm, Simon Pearce, Andrew Pearce, Quechee Gorge and Quechee Segway Tours.
Don’t let a little rain get you down... head over to Green Mountain Rock Climbing or the Killington Art Garage for the day!
INNz + OUTz
The official blog of The Trailside Inn!
Plan Your Getaway
Ready to start planning your Vermont getaway? Contact us for availability and schedule your trip today!