Travel & Leisure recently described Prince Edward County as one of the top places to travel to in the world in their annual list: ‘Cross Montauk, NY, with California’s Napa Valley circa 1970, and you get Prince Edward County, a tiny wine-producing region that’s becoming a haven for creative types.” From Toronto, the county is an easy train ride away. With over 40 vineyards (including Norman Hardie Winery, Closson Chase and Karlo Estates), and now over a dozen breweries, many with tasting rooms, this bucolic land of orchards, vineyards, stunning beaches (Sandbanks Provincial Park is unique in all of Canada), is a mecca for cycling (and eating). On our guided trip, meet our friends along the way and enjoy can’t miss dining, and tasting opportunities that you wouldn’t easily find on your own.
Only Great Explorations:
· Small groups, extraordinary guides, and authentic experiences
· Order off the menu at restaurants you won’t find in guidebooks
· Distinctive, charming hotels too small for larger groups
· We design and operate our own trips so there are only good surprises
37 West St, Wellington, ON K0K 3L0, Canada
Day 1+2
2847 County Rd 10, Milford, ON K0K 2P0, Canada
Day 3 + 4
153 Picton Main St, Picton, ON K0K 2T0, Canada
Day 5 + 6 + 7
| 2026 | 2027 |
|---|---|
| May 18-24 | May 17-23 |
| Jun 1-7 | May 31-6 |
| Sep 7-13 | Sep 6-12 |
| Oct 5-11 | Oct 4-10 |
Trip can start at any date. Self-guided and custom trips also available. Call or email for details.
Trip Size
Total Days
Arrive/Depart
Activity LevelModerate. Average daily distance is 40 - 55 km (25 - 35 miles) with optional route extensions.
TerrainSome gently rolling hills but generally level
CostLand Cost
CAD $3,150
Includes 6B/2L/6D
Single Supplement
CAD $800
Bike Rentals
Hybrid Bikes: CAD $320
Racing Bikes: CAD $420
E-Bikes*: CAD $480
*E-bikes are generally available but are on an ‘on request basis ‘ and will be confirmed on receipt of your booking registration. E-bikes provided are the best rentals available in the region. Our regular fleet of hybrid and race bikes are fun to ride and light and fast, but if having an e-bike will make your trip, we’ll do our best to provide. E-bike rentals are non-refundable.
Prices subject to HST (13%) for trips in Ontario.
Getting There
Your tour starts in the town of Wellington, about 200 km (120 mi) east of Toronto. From Toronto, trains take approximately 1 hr 45 min to Belleville. If travelling by car, it is possible to leave your car in Wellington, where you will be able to pick it up at the end of your cycling trip.
Wellington
Wellington is a lakeside village that is a short cycle away from many of the finest wineries in the County. We meet at 2pm at our first hotel and enjoy a warm-up ride. Afterwards, poke around the shops and cafes of Wellington. After a welcome wine reception, enjoy dinner at a restaurant with a deck overlooking West Lake.
Distance: 28 km; 40 m gain
Wellington
Ride a loop along vineyard studded Closson Road, admiring the restored barns from the 1800’s and tasting wines that are garnering the County acclaim. Visit the Old Third, Closson Chase Vineyards, Norman Hardie Winery and Karlo Estates to name some.
Distance: 36 km; 60 m gain or 43 km; 100 m gain
Milford
From Wellington, make your way first to Bloomfield, with its eclectic shops and cafes, then along West Lake and through Sandbanks Provincial Park, with its sand dunes and stunning beaches before continuing on to our charming accommodation for the night. Dinner will be at a local restaurant in Waupoos.
Distance: 54 km; 80 m gain
Milford
From Milford, you have several options. You can make straight to the beaches of Sandbanks Provincial Park and loop back along quiet roads via Port Milford, where you can stop to visit the Mariners Park museum. Another option is a ride out towards Prince Edward Point to see an incredible Bird Observatory. A shorter option takes you to a secret beach that we will share with you. There is also an option to stop and taste wine on the return trip.
Distance: 32 km; 100 m gain or 55 km; 120 m gain
Picton
From Milford, ride out to Fifth Town Artisan Cheese shop to taste and visit. An add-on option explores Point Traverse and the Prince Edward Point Wildlife Area if you didn’t do yesterday. In Picton, visit the town and settle into our hotel, steps from fabulous restaurants and home to a few craft breweries with tasting rooms.
Distance: 40 km; 180 m gain
Picton
Ride a fabulous loop out to Waupoos, with tasting opportunities at the County Cider Co. and at Waupoos Winery. Lunch will be a highlight at the Lake of the Mountain Resort, with a dreamy setting. Or ride a loop out to Big Island where you can gaze out over Massassauga Point Conservation Area from Robinson Bay. Back in Picton, we’ll dine at an acclaimed restaurant and toast our time in Prince Edward County.
Distance: 40 km; 240 m gain or 56 km; 310 m gain or 60 km; 270 m gain
Depart
We will offer transfers to Belleville by 10 a.m.
This boutique B&B offers a carefully crafted blend of retro farmhouse design and modern amenities. Located a short stroll from superb restaurants, cafes and possibly the best ice-cream store in the county.
Alternate: Augustus B&B
Built in 1870, Jackson's Falls Inn is a former schoolhouse, combining the personalized service of a B&B with the privacy and spaciousness of a country inn. While staying here, you can dine in nearby Waupoos.
Alternate: The Wilfrid Boutique Farmhouse
This lovely historic inn with 13 rooms boasts a superb location steps from downtown. Merrill House is furnished with a balance of fine antiques and artifacts, contemporary art and modern touches. The restaurant has a well-earned reputation as one of the best in Picton.
Alternate: The Manse Boutique Inn & Spa
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