Longed-for Long Weekends: Woodbury in the Litchfield Hills Last Updated: August 2023

Close to home, but far enough away, the quaint town of Woodbury offers weekenders a variety of “Vitamin R” options: rest, recreation, relaxation, and rejuvenation. Woodbury is one “bury” good place to start.
By Stacy Lytwyn Maxwell, contributor Michelle Falcone.

1754 House Inn, Restaurant & Tavern

Amid the pandemic, while numerous businesses fought to stay open in 2020, Michael Bates-Walsh acquired the former Curtis House. He renovated the inn and relaunched it as the 1754 House. Set in western Connecticut’s Berkshires, the house, built circa 1736, first welcomed guests as an inn in, 1754.

Listed on the National Register of Historic Places, whether or not it holds title to the state’s oldest operating inn spurs further discussion. It has, however, been designated as “the state’s most haunted place” by Thrillest, an online media lifestyle website.

Weekenders will appreciate how the owner preserved the inn’s sense of intrigue, character, and charm. Retreat into the lap of Colonial sophistication with a finger on the pulse of comfort and style. Reserve one of the 11 guestrooms in the inn or carriage house where yesteryear reins alongside modern amenities.

What can be more felicitous than spending the entire weekend under the roof that an acclaimed executive chef owns? Chef Michael’s focus on contemporary American cuisine exudes a wonderment of fresh, innovative combinations and infuses the restaurant and tavern with a modern vibe.

After a memorable meal, consider a walk in the one-mile radius of state parks, scenic hiking trails, and views as inspiring as the landscape and seascape watercolor collection by artist Brian Walsh, the proprietor’s father.

Less than half a mile away, Hollow Park offers a flat, one-mile loop trail that meanders along the scenic Pomperaug River. About a mile from the inn, the trail behind the Woodbury Public Library leads to Orenaug Park. It features, among other things, a 1.1 mile moderate hiking trail, a 67-foot, four-inch observation deck and Mesozoic Era dinosaur stories galore. Interestingly, at the Park Road entrance the two pillars are constructed from stones from every state in the United States.

Beeline back to the library to browse the indoor treasures that include a section of local maps and day trip information. Leaving the premises, Main Street itself is a historic district stretch of landmarks and world-famous antique shops. Do not miss the Civil War memorial that salutes the Union Army locals who fought in the war. Tour the gardens and savor a taste of 18th-century life by stepping into one of the earliest historic house museums in the nation, the Glebe House Museum and Gertrude Jekyll Garden. Built in 1740, this Georgian Colonial is listed on the National Register of Historic Places. For a study in architectural comparison, check out the Jabez Bacon House, built in 1760, a stone’s throw away, another Georgian colonial listed on the register.

“Soothe the perturbed, wearied and overworked mind.” Woodbury resident and historian William Cothren wrote these words to describe Orenaug Park over 150 years ago. The passage echoes a timeless truth that is also relevant to weekenders today who visit Woodbury—and end up longing to stay so much longer.