In August, 1896, George and Hannah Adams agreed to lease to Edward D. Reynolds a parcel of land along the west shore of Alum Pond for an annual fee of $10.  In that same year, Reynolds obtained a building contract that approved the construction of "a cottage, with ell, piazza, steps, etc." that was to be completed by October for the sum of $255.  E.D. Reynolds lived in Southbridge, MA, one of eight children of Owen and Nellie Reynolds.  He was born 19 Dec. 1869 and died at the lake on 17 June 1914.  There is no record of marriage or children.

There were only a handful of cottages on the lake when E.D. Reynolds built the house.  The original cottage was named "The Rocks" because of the prominent boulders under its porch.  After the dam was built and the water level raised, these rocks became partially hidden and are now not so visible.  There was a boathouse under the porch with steps leading up into the house.

On July 15, 1914, the property was conveyed to Charles E. Dunton from Spencer, MA, as part of the settlement of the Reynolds' estate.  Charles Dunton was born 25 Dec. 1876 and died 25 Feb. 1947.  He was an original member of the west side Pookookapog Lake Protective and Imporvement Association and was an active participant, performing the secretary duties for many years.  There is no record of any children.

On May 6, 1947 Cora Dunton, widow, sold the property to Charles and Jane Puffer of Longmeadow, MA.  The property remains in the hands of their children, Laura, Lynn, and John Puffer, and is also enjoyed by their children.  There have been many changes and additions to the property over the years, but the original cottage and porch are still intact.  It remains a summer residence and is not winterized.  In 1950, the Puffers renamed the cottage to "Happy Holiday".  As a side note, choosing a name for the cottage took some creativity.  Starting at the dam, the three cottages before Happy Holiday were named as follows:  "Happy Hemlock", "Idle Hour", and "Happy Hour".  Following the theme, Happy Holiday" seemed quite appropriate.  A small cabin was build on the adjoining lot in 1949 where guests could stay and children could play on rainy days.  The premises came with a "2-holer" up under the garage where it remains.  The cottage however had indoor plumbing!  The property is perhaps most known for the painted horse living in a stall of the garage behain the house.  The Puffers enjoy watching folks pass by in their boats, pointing out the horsey to their guests and small children.