1954 Jimmy Johnstone Sr. & Bert Turcotte walked the full 100 acre farm on which Sleepy Hollow now stands and later that year the land is purchased for the purpose of building a golf course.
1959 The course opens for play with Fred Swarbrick as the Head Pro.
1960  The course is named and officially opened for its first full year of golf. The old farmhouse is used as a Change House and Pro Shop.
1961  New Clubhouse is built and opens in September of that year. The original clubhouse was very rustic with solid wood construction, high cathedral ceilings in the dining room and a stone fireplace where the lounge is now located. A 35 acre strip of land is purchased along north side of the club.
1963  Nines are reversed to the layout the club now enjoys.
1967  The Par 3 12th hole is lengthened to the present par 4 and the 13th hole is relocated onto added property.
1968  Swimming Pool and Snack Bar are constructed.
1970  Liquor License is secured.
1971  First formal lease commences at $45,000 per annum over five years. Mike Schurmann becomes Head Pro.
1972  December 16th at 2 a.m. the clubhouse is completely destroyed by fire along with all the club records.
1973  Members and ownership band together to build a new clubhouse at a cost of $320,000. The new clubhouse reopens on November 17th of this year. This year is known as the second “Brown Bag Era” where members brought their own picnic lunches to feast on under the trees and the pond on the 10th hole.
1976  Turf Building is constructed.
1977  Dave Wood becomes Head Pro.
1978  Parking lot is paved.
1983  Development of lots surrounding the course, creating the Estates of Sleepy Hollow residential community.
1989  Bob Kennedy becomes Head Pro.
1990  Hans Marcus purchases Sleepy Hollow Country Club.
1991  Gavin Robertson becomes Head Pro.
1993  Larry MacKenzie becomes Head Pro.
1996  Gary Betts becomes Head Pro.
1997  Construction and remodeling begins on the practice facilities including a new putting green, chipping green and sand trap.
1999 Renovation of the 16th hole.
2002  Renowned local architect, Robert Heaslip is hired to redesign the 1st and 5th holes, as well as a pond expansion and bunker addition on the 11th.
2004 Robert Heaslip is brought in to expand tees and the pond on th 6th hole and helped create the 19th hole.
2009 Internal Clubhouse renovation occurs including the dining room and upstairs washrooms.
2010  Sleepy Celebrates its 50th Anniversary!
2015 Locker room washrooms undego full renovation.
2016 Extensive bunker renovation and restoration of the entire course commences.

Benett Hallas becomes only the 8th Head Professional in the club's history.

Gordon Chilton is appointed as the Head Professional

50 Years of Growth

The summer of 2010 marked our clubs 50th. season. Celebrations, special events and great memories were created as we enjoyed this milestone.

One of the highlights was a June ceremony attended by over 300 club members, special guests and dignitaries. Flags were unveiled, placques were commissioned and a wonderful history of our club was authored by Canadian Golf historian Bill MacDonald.

Here’s what some of our guests said about Sleepy Hollow:


Steve Carrol
Royal Canadian Golf Association

“….the RCGA is thrilled to celebrate 50 years of achievement and success. We wish you continued prosperity”

Jeff Dykeman
Canadian PGA

“….I was invited to play this morning by club member John Simmonds. I went to the website and reviewed the score card proceeded to start licking my chops…six hours later here I am licking my wounds!”

Heather Howell
Ontario PGA

“ Sleepy Hollow has been a loyal supporter of the Ontario PGA and most recently hosted the Senior Summer Championship and the Assistants Summer Championship…….Sleepy is a long time favourite of many of our area professionals.

Dave Mills
Golf Association of Ontario

“I am asked to attend many of these types of functions, however it is evident that the attendance today and the enthusiasm for this celebration shows the members here really love their golf course and facility”

Mayor Wayne Emmerson

Town of Whitchurch-Stouffville

“it is always a pleasure to come to Sleepy Hollow. As a matter of fact I caddied here 40 some years ago. This club provided many jobs for us kids and it still does. You could not find a better organization. The course has gotten tougher and people talk about how courteous and professional the staff here are….professional and friendly”

Mr. Hans Marcus
Sleepy Hollow Country Club

“ it is an honor to have everyone here to share this moment with us. I must thank the members for their compassion and commitment and to our employees for their loyalty and dedication. No wonder so many refer to Sleepy Hollow as the little gem in this part of Southern Ontario”

Gary Betts
Head Professional
Sleepy Hollow

“today we not only celebrate our history, we add to it. And trust that the generations who follow us will have some insight into the legacy that we’ve established and that they in turn will respect this wonderful place and this great game”