ion sneet is space is not sufficient here. Indicate north.

Assessor's Sheets USGSQuad Area Letter Form Numbers in Area

Town Winthrop,MA

Place(neighborhood or village) Cottage Hill

(Great Heactt

Name of Area Cottage Hill/Hillside Ave.

Present Use residential

Construction Dates or Period 1883-1910

Overall Condition good

Major Intrusions and Alterations Mostly intact,

relatively minor modernizations.alterations

Acreage_ approx 2 acres

Recorded By Edward W. Gordon

Organization Winthrop CDO+Historical Comm.

Date (month/year) June, 1994

Massachusetts Historical Commission 80 Boylston Street Boston, Massachusetts 02116

UJ T74 . A

AREA FORM

ARCHITECTURAL DESCRIPTION • see continuation sheet Describe architectural, structural and landscape features and evaluate in terms of other areas within the community.

Cottage Hill, like Winthrop Beach and other parts of Winthrop has suffered f rom alterations in the name of winterizat ion, modernizat ion, etc. The Cottage Hill / Hillside Avenue area represents an intact concentrat ion of res idences exhibit ing character ist ics of the I tal ianate.Queen Anne and Shingle Styles. Highland Avenue bisects this area which also includes parts of Cottage Ave and Prospect Avenue.Th is area is representat ive of housing on Cot tage Hill in its entirety.Like the rest of Cot tage Hill, this a rea is densely built up. Much of this area's charm lies in the picturesque relat ionship between steep, rocky upland terrain and a system of meander ing streets bordered by wood f rame houses. Cot tage Hill 's steep hillsides afford memorab le v iews of Boston Harbor, Broad Sound, Point Shirley and Winthrop from the Beach to the Highlands. This area contains single and two fami ly houses. Most of these houses are covered with c lapboards and/or wood shingles. Al though Cot tage Hill's houses are less stylish and substantial than those of other sect ions of the town that developed more or less at the same t ime (Winthrop Highlands, Thornton Park/Washington Avenue, Cot tage Park etc.), this area's interest lies in the often creat ive approach on the part of late 19th/early 20th century bui lders to sit ing,form and design. Dating to the earliest phase of Cottage Hill 's development is 67 Cot tage Hill Avenue. Built c. 1884-85, th is house is noteworthy for its Queen Anne form and Stick Style surface t reatments. It is essential ly a

HISTORICAL NARRATIVE Q see continuation sheet Explain historical development ofthe area. Discuss how this are relates to the historical development of the community. Cottage Hill is a symmetrical, curving eminence which at a height of 100 feet is the town's highest elevation..

f Cottage Hill is bounded on the east by the ocean and Crystal Bay/Boston Harbor on the west. To the south is * Short Beach and Point Shirley and on the north is Winthrop Beach.Cottage Hill, like all of Winthrop's hills is a ^ drumlin composed of sand, pebbles, small boulders, clay and "unconsolidated till".Overtime, the action of the

ocean has destroyed about half of its length.At the time of English settlement at Winthrop during the 1630's, Winthrop's hills and highlands were heavily forested.Cottage Hill was part of the extensive land holdings of Governor John Winthrop, founder of Boston in 1630. Winthrop evidently spent little time in Winthrop but did build a house on the south side of Cottage Hill. His son Deane Winthrop inherited his father's Winthrop lands and resided for many years in Winthrop until his death in 1703. Winthrop devised a system by which the people of Boston could be alerted to approaching ships.Upon sighting a ship ,he is said to have gone to the top of the hill and hoisted a bush on top of a pole. During the 18th century, various descendants of Deane Winthrop owned Cottage Hill. During the mid 18th century,the most densely settled part of Winthrop was nearby Point Shirley which served as a fishing station and summer resort for well to do Bostonians. By the mid 19th century, Cottage Hill was the private preserve of the John W. Tewksbury, the town's first Selectman. He built a large house on the Crystal Cove side of the hill, near the present Winthrop Yacht Club.During the mid 19th century Cottage Hill was known as Green Hill. During the summer of 1878, Cottage Hill was subdivided into house lots. Initially, a tent city sprang up around the Tewksbury houses and other sections of the hill. Winthrop's first steam train, affectionately called the "peanut train" reached Cottage Hill by 1879. For a short time (1884-85), a standard gauge railroad called the Boston, Winthrop and Point Shirley Railroad skirted the eastern edge of Cottage Hill on a trestle.The Narrow Gauge rail road took over in 1886, with its "loop" completed in 1888. All of these transportation improvements encouraged the development of Cottage Hill. Winthrop historian William H. Clark

j BIBLIOGRAPHY and/or REFERENCES • see continuation sheet ] Winthrop Maps & Atlases-1852,1873,1886,1896,1906,1914 ( Chelsea/Winthrop Directories-1882-1908

Winthrop Directories-1911-1947 William H. Clark's History of Winthrop-(1852) King's Hand Book of Boston, Rural and Puritan Winthrop, p. 115 (1888) New England Magazine, New Series 6 ,1892,pgs.545-549

MASSACHUSETTS HISTORICAL COMMISSION Community: Form No:

Office of the Secretary, Boston Property Name: Cot tage Hil l /Hil lside Avenue

Indicate each item on inventory form which is being continued below.

Architectural Description cont inued sweeping roof l ines, large center wall dormer and charming touches like lunette panel ornamentat ion in l ieu of attic windows. 5 Hillside Avenue (MHC#j }5 )is noteworthy for its unusual form. Here, the house's Prospect Avenue wall is bowed out and surmounted by a great gambrel roof. Textural ly, the weathered wood shingles enhance the unique sculptural qual i t ies of this c.1906 residence. 46 Hil lside Avenue {MHC#% ) is a sol id, well crafted example of 2-family, c .1912 housing exhibit ing e lements of the Shingle and Co lonial Revival styles. 20 Prospect Avenue, built c.1890, is a late example of the Italianate Style with its T-shaped form and intersecting hip and gable roofs with large saw cut brackets at the eaves. The aforement ioned housing is but a representat ive sampl ing of late 19th/early 20th century summer housing in th is area.

Historical Narrative Cont inued "probably the greatest feature of the Eighties in Winthrop was the beginning of a comparat ive ly huge real estate development. In 1882 Great Head, or Cot tage Hill as it was soon named, w a s surveyed for house lots and the owners, Gerry Tewksbury, J.W. Tewksbury and the Wyman Brothers offered their respect ive propert ies for sale." In the Spring of 1883, weal thy Boston leather merchant Wil l iam B. Rice purchased Cottage Hill f rom its aforement ioned owners.Rice was simultaneously developing his lands at Winthrop Highlands. It is interesting to compare the relatively modest, wood vernacular houses of Cot tage Hill with the more self consciously stylish and substantial houses of the Highlands. At any rate Whi tman and Breck were hired to set out the streets over Cottage Hill 's rugged terrain that local skeptics judged impossible to tame. Rice planted 150 trees on the hill and began building a pier 250 feet long into the ocean. The organizat ion of the Winthrop Yacht Club in 1884 undoubtedly served as an attraction for persons consider ing th is area as a summer retreat. By 1886 there were two dozen or so summer residences extant on Cot tage Hill, including 67 Cot tage Avenue ( MHC#3^ ) i n the proposed Cot tage Hill/Hil lside Avenue historic distr ict .Overt ime, Cot tage Hill attracted a solid, middle c lass I summer clientel to its wind swept, sun washed s lopes including Albert P. Crossman, sa lesman (5 Hil lside Avenue, early 1900's), Holl is B. 'Scates, buyer (67 Cot tage Avenue, 1910's), Daley J . Gaude t , carpenter (20 Prospect Avenue, 1920's, MHC#i^ t> )etc. As this great eminence became more and more built up , Cottage Hill superseded Great Head as the name of this drumlin, a l though many locals persist in call ing it Great Head. Wil l iam H. Clark notes that Winthrop became almost exclucively a year round communi ty by the end of World War II. By that t ime, most of Cottage Hill's housing had been winterized. Al though much has been written about Nahant, Newport R.I. and Bar Harbor as summer playgrounds of the rich, little press has been given to working class and middle c lass summer resorts of the Victorian and Edwardian Eras in New England. T h e architectural and historical signif icance of the proposed Cot tage Hil l/Hil lside Avenue Historic District l ies in its largely unspoi led physical evidence of life in a late Victorian Era summer co lony of "ordinary " vacat ioners of relatively modest means. It also indirectly speaks to the profound changes that resulted f rom the introduction of s team rai lroads to Winthrop during the last quarter of the 19th century. Winthrop, long the near private preserve of a handful of famil ies, w a s hence forth opened up to seasonal and permanent commute rs .

Community Property Address

Winthrop.MA Cottage Hill Area

Area(s) Form No

A 37,95,96,170

National Register of Historic Places Criteria Statement Form

Check all that apply:

~J Individually eligible ] Eligible only in a historic district

] Contributing to a potential historic district Potential historic district

Criteria A • B QD C • D

Criteria Considerations: • A • B • C • D • E • F • G

Statement of Significance by Hie criteria that are checked in the above .sections must be justified here.

Cottage Hill (Great Head) Considered eligible as area of summer cot tages developed

beginning in 1883 on steep, hilly upland that had been part of the John S. Tewksbury family's extensive land holdings. This eminence is bordered by the Atlantic Ocean on the East, Short Beach on the South, Boston Harbor on the West and Winthrop Beach on the North. Developed by Boston leather merchant and real estate speculator Will iam B. Rice and set out by Whitman and Breck engineers. Th is district is small and linear taking in both s ides of Hillside Avenue between Crystal Cove Avenue and Prospect Ave, but within its borders are several very well preserved and unusual Shingle Style and Queen Ann residences. This area appears to satisfy criteria A and C of the National Register of Historic Places on a local level.