Fall in Grimsby: Pick-Your-Own Grapes, Escarpment Trails and More
Autumn brings a distinct shift across Grimsby, particularly along the rural upper escarpment and benchland where fruit harvests, changing foliage and quiet country roads come together. The season brings pick-your-own fruit along the ridge, lookout views over Forty Mile Creek, benchland winery stops and warm drinks at cafés along Main Street
Here are a few options to build into a fall day trip.
Lipsitt Orchards & Vineyards
Pick-Your-Own Grapes
While autumn fruit picking across Ontario usually means popular apple orchards, Grimsby’s escarpment benchland offers a rarer option: pick-your-own table grapes. At Lipsitt Orchards & Vineyards, a fifth-generation family farm operating in Grimsby since 1893, visitors can pick Concord and Niagara grapes directly from the vine during peak harvest (September to October). The farm also offers pre-picked apples and plums via its on-site farm stand at this time of year.
Grimsby segment of the Bruce Trail
Escarpment Trails and Lookout Views
Cooler air and changing leaf canopies draw walkers up to the escarpment edge. At Beamer Memorial Conservation Area, two lookout platforms along the Lookout Trail offer wide views over the Forty Mile Creek valley, the town below and Lake Ontario. Access points along the Bruce Trail also connect through forested paths along the escarpment ridge. Free parking is available in the Quarry Road lot, with roadside parking allowed where posted.
Commisso Estate Winery
Benchland Wineries
Autumn coincides with active harvest and crush operations across Niagara wine country. Located directly along the escarpment bench on Kemp Road East, Commisso Estate Winery offers tastings, food pairings and patio views overlooking the vineyard. Just west of the town boundary, Leaning Post Wines provides another nearby benchland stop for small-batch, cool-climate wines.
Harbour Grounds Cafe
Coffee and Warm Drinks
Warming up at local cafes across town offers an easy transition between outdoor stops. Downtown along Main Street, 416 Coffee Co. and Station One Coffeehouse serve specialty espresso and seasonal hot drinks, while Nurish Kitchen prepares traditional Turkish coffee alongside fresh baklava. Harbour Grounds in Grimsby-on-the-Lake offers warm drinks a short walk from the waterfront. Full local cafe listings and locations are mapped in the Grimsby Coffee Shops and Cafes Guide.
Lana Bella Knit & Crochet
Gifts and Supplies for Sweater Weather
Downtown Grimsby also offers a few indoor stops for a fall day out. Newly opened Lana Bella Knit & Crochet off of Main Street carries yarn and supplies for knitting and crochet, along with handmade gifts. The shop also hosts knitting circles in its dedicated sitting area.
