From Crooked Pond to Cottage Country: The History of the Avery Cottages

A Phrase Worth Remembering

Tucked into the Wolfeboro Historical Society's Gazetteer of Wolfeboro is a quiet, easy-to-overlook phrase: the road toward the lake ran "in the vicinity of the Avery cottages."

No map marks them by that name today. No sign announces them. But the phrase points to something real: a cluster of summer cottages that grew out of a working farm on the edge of a lake that most Wolfeboro residents once called something else entirely.

If you rent Crescent Lake Cottage (#516), you will be staying in one of those original Avery cottages, a 1940s-era retreat on the same quiet shoreline where a remarkable Wolfeboro character once kept cows, sold insurance, recorded births and deaths, and slowly opened a road toward the water.

The Man Behind the Cottages

Joseph Clifton Avery was born in Wolfeboro in 1874, and he spent his life making himself indispensable to the town. By 1908, a town directory listed him simply as a "farmer and insurance agent," but that description barely scratches the surface.

Avery served as town clerk, recorded local births and deaths, officiated marriages as a justice of the peace, and collected water bills for the Wolfeboro Water Works. He was president of the Wolfeboro Rotary Club in 1932 and 1933, a position his son Howard would later hold in 1944 and 1945. He also invested in downtown commercial property, purchasing the Trickey-Avery Block in 1920 and the Peavey Block on South Main Street in 1944.

The insurance agency he founded in 1899 still carries a version of his name in Wolfeboro today, more than a century later.

But before any of that civic activity, Avery was a working farmer. Wolfeboro's 1915 tax inventory tells the story in numbers:

• A homestead valued at $3,500
• Substantial fields and pasture valued at $4,000
• A tenement house and several named lots
• Three horses
• Eight cows
• Thirteen head of what the inventory called "neat stock," an older term for cattle

This was not a gentleman's country estate. It was a productive farm, and the land along the edge of the lake was part of it.

A Road That Took 17 Years

On April 1, 1916, the Granite State News reported that Fred C. Dore had purchased a house lot from Avery on Crescent Lake Avenue, "the new street which Mr. Avery intends opening up on his property opposite Green Street."

The town had actually authorized Crescent Lake Avenue back in 1900. Sixteen years passed. Then Avery announced his plans and sold at least one lot. And yet, an October 1917 Sanborn fire-insurance map, drawn just a year later, still labeled the road "PROPOSED ST."

So: authorized in 1900, promoted in 1916, and still provisional in 1917. The cottage neighborhood that grew up along that road appears to have developed gradually, one lot and one house at a time, rather than as a single planned development.

The evidence suggests that Avery was not building a cottage colony so much as subdividing his farm into house lots and letting buyers build their own summer places. The 1915 tax inventory lists farmland and lots but no cottages, which may mean the first houses appeared only after the 1916 lot sales began.

The Lake Had a Different Name

There is one more layer to the story, and it says something about how the whole transformation was marketed.

For most of its earlier history, Crescent Lake was known as Crooked Pond. According to the Wolfeboro Historical Society's research, roughly 90 percent of Granite State News mentions in the first decade of the 1900s still used the older name. "Crescent Lake" became the preferred term gradually, at roughly the same time that roads, house lots and summer cottages were beginning to appear along its shores.

"Crescent Lake Avenue" and "the Avery cottages" sounded considerably more appealing to prospective summer residents than an address at Crooked Pond. The historical name survives today only in Crooked Pond Lane, near the Crescent Lake dam.

Sheep, Ice and Mills: The World the Cottages Were Built Into

What is easy to forget is how busy and industrial that shoreline already was when Avery began selling lots.

Crescent Lake was not originally a recreational destination. Water flowed from Lake Wentworth through the Smith River into Crescent Lake, then toward Lake Winnipesaukee, powering mills at Wolfeboro Falls for generations. The 1917 Sanborn maps show an excelsior factory, woodworking mills, a grist mill, lumber yards, railroad tracks and depots all within walking distance of the future cottage lots.

Goodwin's Basin, the section of Crescent Lake separated from the main lake by a railroad causeway, hosted a commercial ice-harvesting operation from approximately 1895 until 1965. Men cut blocks from the frozen surface each January and stored them for summer delivery while trains moved along the causeway nearby.

And then there was the sheep venture. In 1910, investors created the Crescent Lake Land and Live Stock Company and launched what one later historian called a "great sheep-raising scheme," planning to produce wool, meat and breeding stock along the same shoreline. The Granite State News was enthusiastic. The enterprise was not successful.

Only six years later, Avery was selling house lots on that same shore. The future, it turned out, belonged to cottages.

Staying in the Story: Property #516

The Crescent Lake Cottage (#516) is a 1940s-era retreat that sits right on the water, on the same quiet stretch of Crescent Lake where Avery's road finally reached the shore. Whether it is one of the original cottages associated with Avery's land or a slightly later addition to the neighborhood, it carries the spirit of everything that made this place worth developing in the first place.

The cottage sleeps four across two bedrooms (one queen, two twins) and one bathroom. A sandy beach and swim raft sit just outside the door. The screened porch catches the afternoon light, with southwest exposure over the water. Inside, a fireplace keeps things cozy on cool evenings, and the kitchen is fully equipped for a week of real meals.

Modern comforts have been added thoughtfully. Window air conditioning units mean you can sleep soundly on warm August nights, which Avery's original buyers almost certainly could not. A smart TV and gas grill round out the amenities.

Downtown Wolfeboro, one of the most charming small towns on Lake Winnipesaukee, is just minutes away on foot or by car. Shops, restaurants, the waterfront boardwalk and summer events are all within easy reach.

Browse Property #516 and Check Availability →

The Mystery That Remains

The historical society's phrase, "in the vicinity of the Avery cottages," leaves the full story just slightly out of reach. It is not yet certain exactly when the first cottages were built, how many Avery developed, or whether they were rented, sold or kept in the family. The deeds and old newspaper advertisements that would settle the question have not yet surfaced.

What is certain is that J. Clifton Avery, farmer, insurance agent, justice of the peace and town clerk, looked at his fields beside a lake that people were just beginning to call Crescent, and saw something worth building toward. He opened a road, sold lots, and started something that lasted.

Renting a week at Crescent Lake Cottage (#516) is a chance to enjoy what he imagined, with the addition of air conditioning.

Frequently Asked Questions

What is the history behind Crescent Lake in Wolfeboro?

Crescent Lake was known as Crooked Pond for much of its earlier history, and it supported an active industrial landscape including mills, railroad activity and commercial ice harvesting before summer cottages began appearing along its shores. J. Clifton Avery, a Wolfeboro farmer and civic leader, began selling house lots on land he owned near the lake around 1916, and the cluster of summer cottages that grew up there became known locally as the Avery cottages.

Is Cottage #516 actually one of the original Avery cottages?

It is quite possibly one of the original cottages associated with Avery's land near Crescent Lake Avenue, though the historical record does not yet confirm every detail. The cottage dates to the 1940s, which fits the era when the neighborhood was developing, and it sits on the same stretch of shoreline described in local historical sources as "the vicinity of the Avery cottages."

What amenities does the Crescent Lake Cottage include?

The cottage has two bedrooms, one bathroom, a fully equipped kitchen, a fireplace, a screened porch, window air conditioning units, a smart TV and a gas grill. Outside, guests have access to a sandy beach, a swim raft and a boat mooring. It sleeps four comfortably.

How much does it cost to rent Crescent Lake Cottage #516?

Peak-season weeks are priced at $2,250. Like all Yankee Pedlar rentals, bookings run Saturday to Saturday. Check the listing for current availability and off-peak pricing.

How close is the cottage to downtown Wolfeboro?

Downtown Wolfeboro is just minutes away, making it easy to walk or drive in for meals, shopping and summer events. Wolfeboro is one of the most beloved small towns on Lake Winnipesaukee, with a lively waterfront, local restaurants and boutique shops all within easy reach.

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