Summer Activities

Trailside Inn Summer Activites.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 & 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 freeride 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 singletrack 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.


Road Cycling

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).  Check out the Killington Area Hiking guide for maps and parking info.  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.  Check out the Vermont Brewers Association for more info.

Killington - Long Trail Brewery

Middlebury - Drop-In BreweryOtter Creek & The Shed, Woodchuck Cider & Appalachian Gap Distillery

Brandon - Foley Brothers

Shelburne - Fiddlehead brewery with Fontino’s Pizza attached (Probably our favorite day trip!) & Magic Hat Brewery

Warren - Warren General Store for Lawson’s Finest Sip of Sunshine

Waterbury - Alchemist‘s famous Heady Topper & Focal Banger can be found at Prohibition Pig (along with fantastic food!)

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!


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 & cheese at Sugarbush Farm in Woodstock.  Fresh apples and pies can be found at Mendon Orchards.


Woodstock & Queechee

Update in progress

Billings Farm, Plymouth, Simon & Andrew,


Rainy Days?

Don’t let a little rain get you down.. Head over to Green Mountain Rock Climbing or the Killington Art Garage for the day!