Woodbury Hotels: Which One Was the Curtis House?

Anthony Stoddard built a house on Main Street South before 1736. The Curtiss family bought it, and around 1754 they opened it to travellers. It has taken guests more or less continuously ever since, through one brief pause before the Second World War, and in 2020 it stopped being the Curtis House and became the 1754 House. That single building is most of the story of Woodbury hotels, and the reason so many people arrive asking for an inn that no longer answers to its old name.

There are four places to stay in this town. Not four dozen, four. Woodbury built its reputation on furniture rather than tourism, and the lodging never scaled to match the day-trippers who come for everything the town holds across a day.

Woodbury hotels, all four of them

The 1754 House at 506 Main Street South is the one most people mean and the only one in the village centre. The Milestone Inn is on South Pomperaug Avenue. Woodbury Knoll is out on Tuttle Road and Woodlake is on Clubhouse Drive, both away from the middle of town. That is the entire list.

The 1754 House, formerly the Curtis House

The name change is the practical thing to know. The Bates-Walsh family renovated the inn and relaunched it as the 1754 House in 2020, and search traffic has not caught up: more people look for the Curtis House in Woodbury every month than look for any other business in the town. If someone gives you directions to the Curtis House, they mean this building, and the address has not moved.

Inside, the inn keeps a handwritten list of the previous owners who have held the building over three centuries, which is a more interesting artefact than most historic hotels manage. Rooms have king or queen beds, private baths and individual climate control, and mornings come with coffee and muffins rather than a full breakfast service.

There are two places to eat on site. The 1754 Dining Room is the formal one, opening from late afternoon midweek and from late morning at weekends. The Flat Five is a blues tavern with live music, running Wednesday to Saturday evenings, and the menus across the two overlap heavily. The building also takes weddings of up to 150 people, which is worth knowing if you are booking a quiet weekend and want to ask what else is happening.

The Milestone Inn

Woodbury Knoll and Woodlake

Woodlake is on Clubhouse Drive, also out of the centre. Between these two and the Milestone, the pattern is clear enough: if you want to walk to dinner, the 1754 House is the only address that does it. Everything else means driving into town, which is a five-minute proposition rather than a hardship, but worth knowing before you book.

When Woodbury is full

Four rooms-worth of inventory fills quickly, particularly on autumn weekends. The nearest alternatives sit in the surrounding towns: Washington is about 10 miles northwest and Litchfield about 14 miles due north, both in the same Litchfield Hills country and both with more lodging than Woodbury has.

Those are straight-line distances rather than drive times, because the roads out here wind and a number of miles tells you less than you would like. Treat them as a rough sense of direction rather than a schedule.

One caution about booking sites. Search for hotels in Woodbury on the large travel aggregators and you will get results for Woodbury, New York, home of a large outlet centre, and Woodbury, Minnesota. Several of them also still list the closed Woodbury Ski Area as a local attraction. Check the state before you pay.

Staying here for the antiques

If the trip is about the dealers, the 1754 House is the obvious base, because the thirteen dealers along Main Street run either side of it and the walkable southern cluster starts a few hundred yards away. Staying in the middle of the antiques mile in a building older than every piece of furniture for sale on it is not a bad way to do the weekend.

Time it for Friday to Sunday. The shops keep independent hours and midweek is unreliable. If it is a Saturday, the Saturday market out on Sherman Hill Road opens at 7:30am and finishes at half past two, which argues for arriving Friday night rather than Saturday morning.

Staying here for the sculpture season

Hogpen Hill Farms opens Fridays, Saturdays and Sundays from 4 September to 1 November, and those nine weekends are exactly when rooms are hardest to get. The overlap with autumn foliage in the Litchfield Hills is not a coincidence, it is the reason the season runs then.

Book early for that window, or plan for a different one. Plenty else is running across the nine weeks the sculpture park opens, which is exactly why the rooms go.

Eating where you sleep

The 1754 House is the only one of the four with a restaurant attached, which simplifies an evening considerably. If you are staying elsewhere, Good News at 694 Main Street South is the town's best-known dining room and sits in the middle of a block holding fourteen places to eat. Between the dining room downstairs and the twenty-eight kitchens across the rest of the town, the range is wider than four places to stay would suggest.

For the morning, none of the four does a full breakfast service. The counters that open early are a short drive, and Ayla’s at 6am is the earliest thing in town.