Road trip to Windsor, Ontario
Taking your game on the road is one of the great pleasures of golf. Whether it’s a buddy trip or a couples outing, the opportunity to visit other parts of the country, sample some terrific golf courses and pamper yourself for a few days should be on every golfer’s calendar.
Our destination this week is Windsor, Ontario, the heart of Essex County and directly across the river from Detroit. It’s just four hours from the GTA – a straight shot west along the 401. Leave in the morning and you could easily have time for 18 holes in the afternoon.
Windsor ticks a lot of boxes when it comes to road trip destinations – everything from ease of travel to excellent golf courses to great value but one that stands out is the geography. As a border city, you’re really getting two cities in one. With Detroit right across the river, literally just minutes away by bridge or tunnel, you can add everything that city has to offer too.
One more thing about Essex County to consider is that it’s the southern most point in the country, on a latitude with Northern California, and enjoys a longer season than we generally see in the GTA. Typically, that means a couple of weeks at both ends of the season when they’re playing golf in Windsor and we’re not.
Of course, a road trip to Windsor is fun any time. My most recent trip was last fall, and the golf was terrific as usual. I’ve highlighted five courses that should be on your list if you visit the city. Two of them are relatively modern, while the other three are 100 years old. All five of them were included on our 2025 list of the Best Value Golf Courses in Ontario.
The Golf Courses
Ambassador Golf Club
Windsor, Ontario
18 holes / Green Fee: $62-72 Walking
Ambassador is the region’s top-ranked public course and earned distinction as Ontario’s Best New Course when it opened in 2005. It has been a perennial inclusion on any Best Value listings since. The course was designed by Tom McBroom, one of Canada’s top modern architects, and features a par‑71, 18‑hole championship layout stretching nearly 7,000 yards, built on gently rolling terrain with elegant bunkering and large sloped greens. Water features come into play on several holes. Noted for its memorable par 3 holes and pristine conditioning, Ambassador should be included on any road trip itinerary.
Roseland Golf Club
Windsor, ON
27 Holes / Green Fee: $60 Walking / $80 Riding
Canada’s only municipal Donald Ross golf course (est. 1926), Roseland rests in the heart of Windsor. An elegant layout loyal to its original design, its terrain may be flat, but its greens provide elevation and movement. Typical for Ross designs, putting surfaces are generally pitched from back to front, with multiple tiers and the odd false front contributing to the challenge. The depth of well-placed greenside bunkers adds to the defence of par. The course’s parkland style incorporates mature trees, gentle elevation changes, and natural corridors that create a timeless, traditional aesthetic. Roseland also features a nine-hole par-3 course that offers a more stress-free walk in the park.
Note that Ambassador and Roseland are just minutes apart and offer a convenient option for anybody looking to schedule 36-a-day.
Sutton Creek Golf Club
Essex, ON
18 Holes / Green Fee: $59-72 Walking
Sutton Creek (1990), located just south of Windsor in Essex County, is an 18‑hole, par‑72 parkland layout that plays hard and fast with lightening quick greens. And if that’s not enough to keep you on your toes, 60 bunkers, seven expansive ponds and the county’s McLean Drain, which winds through the course, all add to the need to be precise. Water embraces the final two greens, including the signature 18th, a reachable par-5 where the putting surface arcs into a pond, with two bunkers also defending par.
Erie Shores Golf & Country Club
Leamington, ON
18 Holes / Green Fee: $56-60 Walking
Erie Shores (1926) started celebrating its centennial a little early with the grand opening of its new clubhouse last year. This mature, tree-lined routing is about 45 minutes from hotels in Windsor and features gentle elevation changes and panoramic views of Lake Erie at the start and finish of both nines. Although just 6,145 yards from the tips, the proximity to the lake means that wind can be a regular factor. Quiet, relaxing and friendly, Erie Shores has the feeling of a classic, members’ club.
Kingsville Golf & Country Club
Kingsville, ON
27 Holes / Green Fee: $60-65 Walking
Celebrating its 100th anniversary last year, Kingsville is just a 30-minute drive from Point Pelee National Park, home to more than 200 species of birds and other wildlife, as well as natural historic elements unique to the region. Laid upon rolling terrain—a rarity in Essex County—this is a property that provides a great canvas for golf course architecture. There are three nines to choose from at Kingsville. The White course opens with a series of raised tees and greens, followed by five flat holes, before closing with more great movement at the par-3 9th. The Red course makes for the easiest walk, while the Gold course gets the gold medal as the most visually impressive and elegant of the three nines.
Note that Erie Shores and Kingsville are just 25 minutes apart, offering another convenient opportunity for 36-a-day.
Where to Stay
There’s a long list of brand name hotels along the main routes leading to the tunnel and bridges to the U.S. Windsor isn’t an expensive city and it’s still possible to get a room for a bit more than $100 per night. They’re all close to golf too with Roseland and Ambassador just 8-10 minutes away and the other three courses within 30-50 minutes.
Another option is to stay at Caesars Windsor Casino. It’s right next to the tunnel and only adds about five minutes travel time to the various golf courses. Current rates start around $150 per night. Obviously, there’s the attraction of the casino itself but the tunnel spills out across the river into the Greektown section of Detroit, which has plenty of restaurants and pubs, major league sports and three more casinos, all less than 20 minutes away.
Where to Eat
On a road trip, it’s easy to fall into the trap of “anything on a bun with fries,” so if you can get a solid recommendation from a local, that at least gets you beyond fast food and chain restaurants. On our trip, we enjoyed The Keg one evening, which is always a solid choice. For other local favourites, I asked our Good Thinking Golf Performance Coach Jeff Boismier for some top suggestions. Jeff is a long-time resident in the region and he offered the following:
For Italian food, including pizza: Picolos Pizza & Pasta House
For steak, chops and seafood: Take 5 Bistro
And for a great sports bar: The Goat Tap & Eatery Sport Bar, which actually has 3 locations in the Windsor area.
Our friend ChatGPT, offered this suggestion: Neros Steakhouse is widely considered the best upscale option for steaks and river views, while Spago Trattoria offers well-regarded Italian cuisine. Both are at Caesars Windsor Casino.
Other things to do
The Windsor Casino is usually a top draw for road trippers. There is also sightseeing along the Detroit River, including the new (but not in use yet) Gordie Howe Bridge and a number of wineries in the area. In the summer months, beaches on Lake Erie or Lake St. Clair are very popular, as is Point Pelee National Park. All are less than an hour away.
Detroit is home to teams in all four major league sports: MLB Tigers, NFL Lions, NBA Pistons and NHL Red Wings. If you like automotive history, the Ford Museum is definitely worth seeing.
Enjoy your travels!
