Check Out These Decked-Out Holiday Houses

It’s one of the most interesting — and oldest — places in Westport. I’ve lived here my whole life, yet never been inside.

Adams Academy — the low-slung yellow building on North Morningside — was the spectacularly named Ebenezer Adams’ private school from 1837 to 1867. He taught over 600 students — including (rare for the time) girls. Most of the graduates — male only, of course 😦 — went on to Yale.

After Adams sold his academy, it served as a public school, town park, home for the  needy and town offices.

Now restored, it’s back to a 19th century schoolroom.

Adams Academy (Photo/Michael Mombello)

It’s rarely open. But next Sunday (December 9), it’s one of 5 stops on the Westport Historical Society’s 32nd annual Holiday House Tour. Ebenezer and his daughter — well, WHS volunteers dressed as them — will be there to greet guests.

The tour offers a peek inside some of Westport’s most historic structures. It combines our natural voyeurism curiosity with our intrigue in our past — and our love for New England-style holiday decorations.

Each stop on the self-guided tour includes WHS docents, explaining how people of the period celebrated Christmas and New Year’s. Halls (and more) will be decked with boughs of holly (and much more).

The event begins at the Historical Society’s own Wheeler House home on Avery Place. Built in 1795, then remodeled in the 1800s in Italianate style, it’s listed on the National Register of Historic Places.

Wheeler House — the Westport Historical Society’s Avery Place home — in a painting by famed local artist Stevan Dohanos.

Wheeler House — dressed in Victorian splendor — is complemented by the only octagonal-roof cobblestone barn in Connecticut. It will be open too, showcasing the fantastic, intricate wintertime train set that for years thrilled shoppers at Swezey’s Jewelers on Main Street.

The  Goodsell-Grumman Toll House dates back to 1760. It originally stood on Catamount Road, but when a private highway — Easton Road — was built in 1817, it was moved to its present location there. It’s one of the few remaining saltbox-style homes in Westport.

The Goodsell-Grumman Toll House on Easton Road. (Photo/Michael Mombello)

Two other Holiday House tour homes are in Southport. A 1673 (!) colonial saltbox — one of the oldest still standing in Fairfield — features an original entryway staircase, exposed beams and massive fireplaces.

The John Osborne House, Kings Highway West in Southport. (Photo/Michael Mombello)

A converted barn, built in 1705, has original framing and reclaimed period wood for all walls and floors. This house sits atop a burial ground from the Great Swamp War. In the 1940s, it was used as an artists’ studio.

The Osborne Barn, Oxford Road, Southport. (Photo/Michael Mombello)

There’s a lot going on this season. It’s not easy to fit a House Tour into your schedule.

But there’s no better way to get in the old-time holiday mood.

Just ask Ebenezer Adams.

(The Westport Historical Society’s Holiday House Tour takes place Sunday, December 9, 11 a.m. to 4 p.m. Click here for tickets.)

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