Weekend in Windsor
Trip Overview
This compact weekend marries Windsor's revived riverfront with its rising food-and-drink quarters. You'll glide past Detroit's glass towers on a sunset kayak, spin the Chrysler Canada Greenway through Carolinian woods, and graze from pierogi trucks to Neapolitan ovens. The tempo stays easy, early starts dodge summer humidity, lazy lunches linger beneath maple shade, and nights end with craft cider on walkable patios. Everything sits inside a 15-minute radius, so flip-flops replace wheels once you're settled.
Pace
Moderate
Daily Budget
$130-190 CAD per day
Best Seasons
Late May through mid-October for patios and river sports. Winter lights along the river still dazzle from November to March
Ideal For
Weekend escapees from Toronto or Detroit, Couples seeking skyline romance, Cyclists and paddle-boarders, Craft-beer hunters
Day-by-Day Itinerary
A complete plan for every day of your trip
1
Riverfront Wheels & Riverside Flavours
Downtown Windsor & Riverfront Trail
Cycle the Chrysler Greenway, lunch on wood-fired pizza in Walkerville, then watch the Detroit skyline ignite from your kayak.
Morning
Bike the Windsor Riverfront & Chrysler Canada Greenway
Rent a hybrid at City Cyclery on Pelissier Street and glide east along the river. You'll catch lake-mist off the Detroit River as freighters drift past Coventry Gardens' sculpted beds. At the Little River Extension, maple canopy dapples sunlight onto the crushed-limestone path while you roll 12 km south toward the Jack Miner bird sanctuary.
Reserve day before online. Locks and helmets included
Lunch
Naples Pizzeria on Wyandotte
Afternoon
Walkerville Heritage Walk & Willistead Manor
Pedal back through Walkerville's red-brick lanes where Hiram Walker's whiskey empire began. Pause at Willistead Manor, half-timbered Tudor ringed by oaks, then slip into Walkerville Brewery for a flight of crisp lager beneath the rattling steel rafters of the 1890 carriage house.
Drop-in; brewery tours top of each hour
Evening
Sunset paddle with Windsor River Cruises
Two-hour guided kayak west toward the Ambassador Bridge. City lights shimmer on black water while the guide points out the glowing Renaissance Center towers
Where to Stay Tonight
Downtown around Riverside Drive (Best Western Plus Waterfront Hotel)
Rooms face Detroit skyline; 5-minute walk to dinner and ferry dock
See all Windsor accommodation options →Bring a dry-bag for your phone, river spray hits when freighters pass.
Day 1 Budget: $170 CAD
2
Market Mornings & Island Afternoons
Peche Island & Via Italia
Start with perogies at Saturday Farmer's Market, ferry to Peche Island for a picnic swim, then graze through Erie Street's patios.
Morning
Windsor Farmer's Market & Peche Island ferry
Under white canvas tents on Pelissier Street, vendors fan charcoal smoke over pierogi stalls and jars of local honey shine gold. Snag potato-onion pockets and board the 10 am pontoon shuttle from Lakeview Park Marina. Ten minutes later you're stepping onto Peche Island's pebble beach edged by silver birch and sumac.
Tickets at marina kiosk. Check windsorweather for wave warnings
Lunch
Pack the market pierogi plus fruit from the orchard stall. Eat on the island's south shore with Detroit's Renaissance Center framed by cattails
Afternoon
Via Italia patio crawl
Walk 20 minutes from the marina to Erie Street. Terracotta planters spill lavender onto the sidewalk outside Taloola Café where espresso arrives with lemon zest. Continue east; Mezzo Ristorante's patio smells of garlic scape butter while the bar pours Ontario gamay. Wrap at Carrots N' Dates smoothie bar for cold-pressed ginger lemonade.
No reservations needed except Mezzo for dinner
Evening
Craft-cider sunset at Windsor Riverfront Plaza
Grab a tall can of Motor City Brewing cider from the riverside kiosk, settle onto Adirondack chairs facing the Ambassador Bridge lights reflecting in slow-moving water
Where to Stay Tonight
Same downtown hotel (Extend stay or check out and head to Detroit-Windsor Tunnel if driving home)
Next-day departure via Gordie Howe Bridge is 12 minutes west
See all Windsor accommodation options →Free parking after 6 pm on Erie Street. Plug meters accept credit cards earlier.
Day 2 Budget: $155 CAD
Practical Information
Everything you need to know before you go
Getting Around
Walk or bike once downtown. The Riverfront Trail links every stop. Lyft and local Transit Windsor buses fill gaps. If arriving by car, municipal garages on Pelissier and Chatham cost less than hotel valet.
Book Ahead
Saturday ferry to Peche Island, sunset kayak with Windsor River Cruises, and any dinner reservation at Mezzo Ristorante
Packing Essentials
Light windbreaker for river breezes, reusable water bottle (public fountains along trail), swimsuit for Peche Island dip, bike shorts if you'll cycle
Total Budget
$325-345 CAD for the weekend excluding accommodation
Customize Your Trip
Adapt this itinerary to your travel style
Budget Version
Skip hotel for HI-Windsor hostel ($35 CAD bunk), picnic both days using market groceries, rent city bike instead of hybrid ($20 CAD), take free Riverfront fitness classes instead of paid kayak.
Luxury Upgrade
Stay at Caesars Windsor Augustus Tower suite with river view, book private Peche Island pontoon charter ($200 CAD), upgrade dinner to Nero Restaurant's chef's table with paired Ontario wines.
Family-Friendly
Swap bikes for four-seat surrey from City Cyclery, hit Adventure Bay Family Water Park after market, dine early at Giovanni Caboto Club for kid-friendly pasta before fireworks on Riverfront Canada Day weekend.
Book Activities for Your Trip
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