Orangeville Tree Sculpture

Visitor's Guide

Only steps from Toronto are a series of quaint villages and picturesque hamlets. Shop all morning in the unique boutiques, tour artist studios in the afternoon, enjoy the fine dining of our bistros and relax by the fire with a night cap at our pubs.

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Visitor's Guide


Escape hectic schedules and relax with friends and family in the quality ambience and comfort offered by the Hills of Headwaters accommodations. Our region offers charming, cozy inns and bed and breakfast retreats, luxurious resorts and full-service conference facilities. Whether you are taking your business on the road or headed north for some family fun, the Hills of Headwaters hosts are pleased to make your stay a memorable one.

Agriculture & Farm Fresh
Stunning scenery is but one reason to visit the Hills of Headwaters. As modern society yearns to re-connect with this part of our heritage, agri-tourism has enjoyed a growing popularity. Within the heart of the Hills of Headwaters, there are an assortment of farm markets and pick-your-own operations that allow visitors to experience first-hand the awesome freshness that can be savored only when ripe produce is harvested fresh from the field.

Arts, Culture & Heritage
Restore your zest for a culturally rich life by visiting The Hills of Headwaters. Professional entertainers provide live theatre, musicals, and quality concerts for all ages and interests. Patrons of the arts will appreciate the diversity of artistic mediums offered to enhance their appreciation of creativity of originality. History comes to life at the Dufferin County Museum and at the region's many historic villages and towns.


When you’re in the Hills, the attractions almost always involve culture or the outdoors.  Visit a heritage museum, hike our conservation areas or ride the rails on the Credit Valley Explorer tour train.

Banquets/Meetings/Trade Shows
Planning your special day or a meeting that will excite your team is easy in The Hills of Headwaters. Our range of facilities will fit any size party and our hospitality industry services will make any event success. We can help every occasion become an unforgettable event.

Business Services
Acquaint yourself with the world of professional and creative services that exist in the Hills of Headwaters. The diversity of our business community is appreciated by visitors and residents alike: personal health care, printing, graphic design, money management, marketing, consulting and wine events, to name just a few.

Community Services
In the Hills of Headwaters region there are many organizations that can assist you in many aspect of your life.

Dining & Catering
Experience The Hills of Headwaters and its diverse dining opportunities. From affordable entertainment for kids to gourmet fare in exquisite ambience, our pleasant café's, cozy pubs and quaint tearooms have something for everyone. If entertaining from home is the event, our Headwaters Country gourmets will delight your guests while you relax and enjoy the evening. Mouthwatering meals made from the freshest of ingredients served up with our heartfelt Headwaters hospitality!

Family Fun
Summer break in the Hills of Headwaters is never boring.  Whether you are a local or just passing through there is plenty for the whole family to see and do in our region.

Festivals & Events
The Hills of Headwaters offers a wide range of special events for every visitor to enjoy. Concerts, festivals, fairs, agricultural events, arts and culture, and even home design seminars.

Just a short hour’s drive north of Toronto, you’ll find the Niagara Escarpment’s undulating terrain creates challenges for golfers at all levels. The varying elevations and spectacular views are typical of the courses in the Hills of Headwaters.
Here in the Hills of Headwaters you will find an outstanding golf experience: challenging and diverse course and practice options; a casual and relaxed atmosphere where golfers feel immediately welcome the moment they arrive; exceptional customer service; and a wide array of regional attractions and amenities to enhance your golf outing!

Health & Well-being
The Hills of Headwaters offers a broad range of spa and wellness facilities that cater to physical, emotional, intellectual and spiritual health. An extensive variety of treatments are available, including facials, body wraps, pedicures, massage therapy, aromatherapy and much more. Spoil yourself and come luxuriate at one of many spas. There is something for every taste, lifestyle and budget.

Home & Garden
Let our Headwaters designers and builders help you to create your dream home. Professionals with experience, know-how and excellence in customer care.

Real Estate
Once you’ve discovered the Hills of Headwaters, you’re not going to want to leave!  Any one of our talented real estate agents would be pleased to help you find your dream home.  Inspired to build a new home?  Let one of our new home builders help you get creative.


Breathe in the fragrant country scents of spring, bathe in the sunny days of summer, delight in the colourful hues of fall, or feel the crispness of winter snow. Discover our numerous trails, unique with natural life in all seasons. There is something for everyone, from bird and wildlife enthusiasts, photo-buffs, serious backpackers or day hikers, cross-country skiers, mountain bikers and snowmobile riders.

Inviting shops and boutiques set in country villages are havens for exploring treasure hunters. The Hills of Headwaters offer everything from unique and affordable to traditional or trendy. You'll find apparel for all ages, seasons, and occasions, as well as great ideas for special occassions, decorating, and culinary delights.

Towns & Villages
The region's rivers have shaped and determined the history and development of the Hills of Headwaters. While many of the mills established to harness waterpower are gone, the settelements that formed around the mills live on as scenic towns and villages where quaint shops and tearooms welcome visitors.

Events Calendar

Featured Events

Corn Flower Exhibit - Part of Our Canadian Heritage
Mar 13 - Dec 15, 2011
Dufferin County Museum and Archives

Caledon Farmers' Market - Bring Your Pet Day
Jul 14, 2011
Town of Caledon

Cuisine Art
Jul 16 - 17, 2011
Alton Mill - Galleries & Art Studios

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