Featured, Local News

100% Inn – Trailside Inn owners succeed with market niche


After five years as minority owners, Ann and Joshua Eckler celebrate purchasing Trailside Inn on Route 100 north in Killington from former partner, Joe DeSena.

By Polly Mikula

It’s been about five years since Joshua and Ann Eckler first arrived at Trailside Inn – a venture they began as minority owners with Joe DeSena, who had purchased the inn three or four years earlier. Now, the Ecklers are the sole owners, having recently finalized paperwork to buy DeSena’s share in the property located just off Route 100 north in Killington.

“This March will mark five years for us,” said Joshua Eckler. “It was a real benefit to partner with Joe in the beginning, but so much has changed now and we’re ready to do this thing on our own.”

Joshua said they struck a deal to purchase DeSena’s share in the business last year, but finalizing the purchase took longer than they’d hoped. “We got the go-ahead last March… It’s hard to get even 10 minutes of Joe’s time. He’s very busy, has been living out of the country, and is [understandably] preoccupied with bigger ventures, like Spartan. This will be one less hassle for Joe.”

Regarding the purchase price, Joshua said, DeSena “just didn’t want to lose money on his investment, he was very fair to us,” adding. “He knows that we’re strong enough financially, now. In fact, he’s even doing some of the financing. It was a good deal for both of us. It was the right time, we had the first four years to get to know what really worked and to have Riverside and his other businesses working closely with us, but now it’s different. We’re excited to have a more equal partnership with Riverside. We really operate independently now and have found other niches that we’re pursuing successfully.”

The niches, the Ecklers explained, are private events. Trailside is uniquely suited for corporate retreats, large family reunions and weddings. “It’s rare to be able to rent out an entire place that can sleep 100,” Joshua said. “Private events are our thing.”

For 2019, March is sold out to corporate events and this summer is sold out for weddings with 21 booked. Fully 60-70 percent of their business in 2019 will come from private events – mainly corporate retreats and weddings, Joshua said.

Trailside is not open mid-week, unless booked for a private event. Between corporate retreats and weekend skiers through the winter, the Ecklers keep busy. Plus, “it’s difficult and costly to get staff mid-week,” the Ecklers explained.

Joshua met DeSena as a participant in his Death Races years before moving to Trailside Inn. “I used to workout with Joe and Andy [Weinberg] daily, we were good friends,” he said.

Joshua and Ann took over management and operation of Trailside as minority owners in 2014. DeSena and another friend had bought the place from the bank in 2010-2011, Joshua remembered. “It had a 1977 interior with green shag carpets,” he said. “And the lodge had sat empty for three years prior to their purchase – it had been through three winters without heat and all the pipes had burst.”

Then Tropical Storm Irene came through and flooded the basement.

DeSena did major renovations on the Inn. “He renovated it 90 percent,” said Joshua.

“Now we’re just doing the finishing touches, such as updating the bridal suite and tile work and the game room,” Ann explained. “We’ve done some wedding upgrades too, like new floor in the tent space and adding 10 feet to the tent.”

Just three years ago there had never had a wedding on site at Trailside Inn; now they’re sold out for 2019.

“We’ve probably invested $40-$50K into weddings over the past few years,” Ann said, adding that the investment has been well worth it. “We’re definitely expanding but we’re aiming to grow at a sustainable rate.”

With the buyout from DeSena, the Ecklers are looking forward to having more autonomy.

Since they got the go-ahead to purchase, the Ecklers have rebranded the inn, switched booking sites and redone their website. Other upcoming projects include renovating a few of the remaining bunkrooms and the game room downstairs.

“Maintaining our high occupancy is important, but we just need beds, not necessarily queens,” said Joshua. “The average age of guest for corporate retreats is 28-45.”

The Ecklers said they classify themselves as a “boutique hostel” sleeping 100 people on-site in 37 rooms. Of those, 28 are private rooms in the main inn, plus a separate guest house with two apartment units, the Barn (sleeps 12) and the Loft (sleeps 10).

Trailside Inn does not have a kitchen or bar; so groups can bring in their own food and beverages, have meals catered there or eat out.

“Our groups usually opt for a combination, it’s nice to be able to customize the offering for the specific groups need,” said Joshua.

The Inn features a large common area with a huge open fireplace, couches and large wooden tables. Downstairs it offers a game room.

“The game room is aimed at 30-40-year-olds with a beer in their hand,” said Joshua. “It’s mostly used as a late night hang out.”

The Ecklers plan to add a bathroom downstairs off the game room, update some games, seating options and finishes, so it can be a self-contained social space.

The Trailside Inn began as a hostel for through-hikers.

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