Fairways & Fall Colours

Begin your weekend by taking in the rich fall colours on the scenic fairways of Osprey Valley Golf Course, and experience the PGA’s newest Tournament Player’s Club member. Home to the summer Osprey Valley Open, this world-class course boasts equally stunning fall vistas on each of the 18-hole Hoot, Heathlands and North links. After your game, explore the back roads on your way to Downtown Orangeville. Check in at the Best Western Plus Orangeville Inn & Suites and relax in your spacious suite, or lace up your walking shoes and experience the Historic Downtown Orangeville Walking Tour. Savour a tantalizing meal at RustiK Local Bistro, or Soulyve Caribbean Fusion, two of Orangeville’s many culinary gems. After a good night’s sleep, wake up to the complimentary hot breakfast at the Best Western Plus. For a crisp morning stroll, drive to the Island Lake Conservation Area and explore picturesque footbridges and tree-lined trails bursting with brightly coloured foliage.

Fore! Fine Dining & Fairways

With premium courses across the region, Headwaters offers some of the best golf in Ontario. Designed by architect Rene Muylaert, the 18-hole Caledon Golf and Country Club is set in the beautiful Caledon hills. The course offers an enjoyable play for any level of golfer, along with a stunning view of the course from the hill-top clubhouse and patio. After a day of golf in the vibrant hills of Caledon, check-in to one of the finest accommodations in the region, Millcroft Inn & Spa. This historic inn is located on a beautiful mill pond full of fish to feed as you sit on the patio overlooking the Credit River; there are a variety of styles of accommodation plus a European style spa on the property, as well as beautiful hiking trails winding around the sprawling property. While in Alton, head over for an afternoon at the Alton Mill Arts Centre and take a stroll through the galleries and one-of-a-kind shops of this historic mill. The 2018 Headwaters Art Festival takes place from September 20th to October 8th, 2018. Now in its 22nd year, the festival is a must for art lovers, offering a juried art show and sale, blues party, and even a movie night. Worked up an appetite? Visit Ray’s 3rd Generation Bistro-Bakery, a favourite amongst locals and visitors alike!