Wayside Inn prepares for big expansion

“Given these changing times, you have to think outside the box,’’ said Cowden, “So we’ve done a lot of that.’’

Leo Xarras, a partner at OS Sudbury LLC, which owns the Clarion Carriage House, said the inn will be much more upscale when renovations are complete.

“The Wayside Inn is a very successful food and beverage venue, and I think the hard part for them has been the lodging component - not having the additional guest rooms to bring in the wedding parties and everything else,’’ said Xarras, whose company also owns the Castle Hill Resort and Spa in Ludlow, Vt. “When renovated, the Carriage House will do just that.’’

Neither Cowden nor Xarras would discuss financial details of the pending deal, which could begin another chapter for the storied Wayside Inn.

Reputed to be the oldest operating inn in the country, it looks like it was pulled from the canvas of an 18th-century painting. Its innkeepers over the years have expanded, adapted, and one time even rebuilt the inn after fire gutted it in 1955. The constant has been that, for three centuries, the Wayside Inn has survived war, disaster, and even the occasional economic recession.

Cowden started making changes quickly after he was named innkeeper in September. A gift shop was converted into a bake shop, turning out breads, cookies, and scones using flour ground at the inn’s on-site mill. He plans this year to turn the bake shop into an New England general store with penny candy and fresh produce. Cowden also renovated the inn’s ballroom and plans to add outdoor fire pits for dinner and cocktail hours. With the down economy, Cowden also added dinner specials, package room-meal specials, and a free country-style breakfast for all overnight guests. The total cost of the improvements, Cowden said, was about $30,000.