12 Prettiest Downtown Strips In Ontario
Canada's province of Ontario brims with small-town adventures waiting for you to explore. Although the province is home to both the national and provincial capitals, it is the small towns in between that make it worth traveling. From the banks of flowing rivers to the shores of the Great Lakes and the heart of wine country to the tip of the mighty Bruce Trail, get ready to discover 12 of the prettiest downtown strips in Ontario.
Port Hope
Port Hope overlooks Lake Ontario at the mouth of the Ganaraska River, flowing like a silver ribbon at the foot of the downtown strip. The main street's gentle slope leads to a quaint bridge, creating an enchanting view. Historic buildings of red and yellow brick complement the elegant cast-iron streetlamps. Shoppers delight in the diverse boutiques and enticing window displays. Avid readers browse the titles at Furby House Books. Treasure hunters spend hours poking around Retrospective, whereas interior design mavens find statement pieces at Penney & Co.
Local eateries like The Thirsty Goose embrace the craft brew trend. Dine on homemade classic pub fare and sample their rotating selection of microbrews. Prefer a more upscale dining experience? Trattoria Gusto at the Waddell Hotel is sure to please. Tuck into innovative Italian cuisine, sample vintages from an impressive wine list, and imbibe in seasonal artisanal cocktails. The Waddell is a Port Hope landmark, claiming the corner at the foot of the main strip. Its lavish, period-inspired hotel rooms boast splendid river views as the perfect end to your visit.
Paris
Snuggled at the junction of the Grand and Nith Rivers, Paris is a one-of-a-kind experience. Historic buildings backing onto the river have a sense of the Thames in London. A bridge accented by colorful flower baskets is a cheerful welcome to the downtown strip. The main street features examples of period architecture with distinct brick chimneys, giving the town its European flair.
The turret at the Arlington Hotel is one of the most notable sites. The building sports a yellow brick façade, arched windows, and several rooftop gables. Intricate ironwork and four elegant arches accent the historic front terrace. If you can only choose one place to dine, the rooftop patio at Stillwaters Plate & Pour is the place to be. The tantalizing local dishes are all the more enjoyable thanks to unmatched river views.
Paris Bakery's small-batch bakes fulfill your sweetest desires. As a popular town hotspot, in-the-know locals always pre-order their favorites. It is no wonder the bakery has been operating for almost a century. Off the beaten path, Wincey Mill mixes culinary and cultural experiences. This year-round market hall features an intriguing range of local goods, from food to crafts.
Picton
Picton is one of two main downtown areas in Prince Edward County on Lake Ontario’s Bay of Quinte. Featuring brick façades, ornate rooftop detailing, and elegant wood-framed windows. Details like the yellow and white striped awning at The Yellow Studio add creative flair.
Local fashion boutique owners join forces for June's annual Picton Fashion Week. Fashionistas arrive to check out the trends and enjoy a unique, immersive experience. Indulge your inner fashion fanatic at diverse boutiques, including City Revival and Magpie.
Eateries showcase the talent of local chefs, wineries, and breweries. Whether it is pizza and beer at 555 Brewing Co. or tapas and wine at Bocado Restaurant, the main strip will feed you well. View a film at the retro Regent Theatre or show off your moves at a Vic Social Dance Party. The Lake on the Mountain area is home to an Ontario natural wonder, a small lake sitting 200 feet above Lake Ontario. The area also offers unmatched views of the lake on one side and the bay on the other. If it feels too crowded, the Lake on Mountain Brewery has a secluded beer garden and tasty flights.
Cobourg
Cobourg's sleepy lakeside town comes alive in the summer with the arrival of beach lovers. However, the historic downtown is a year-round attraction.
Historic Victoria Hall stands three stories tall with imposing Corinthian columns and a large stone-faced central pavilion. A massive cupola, complete with a clock tower, is the crowning glory. The third floor is now home to the Art Gallery of Northumberland. If you fancy art, take in the exhibitions and permanent collections.
Main Street clothing shops are all about eclectic vintage collections at Northern Vintage Vibez and Little Underground. Fabled Bean is a coffee addict’s destination with an assortment of coffee, sandwiches, and breakfast items. Eclectic shop Lolly Gag encourages visitors to sip coffee, munch scones, and shop for unique finds. The El's intriguing menu features globally inspired dishes made with local ingredients. It has a swank, upscale feel yet invites guests to sit back, relax, and sample shared plates. Jack’s Barrel House offers a warm welcome along with live music, tempting casual fare, and a generous drinks menu. Make your way down to green and shady Victoria Park, or walk down to the sunny, white sandy beach, ideal for tanning, swimming, and toe-dipping.
Unionville
Main Street Unionville has long been a destination for Toronto residents in need of a reviving dose of small-town charm. Colorful clapboard siding and gables add a whimsical feel to the storefronts and restaurants, made all the more charming with the addition of a red-bricked roadway.
The town invites you to wander its notably upscale boutiques. Cigar Bodega and high-end vintage designer consignment boutique Susannah are perfect examples of the exclusive feel of the main strip.
The global cuisine includes Honoka Japanese Dessert Café, authentic Indian at Ambiyan, and a taste of Korea at Pig & Chick. Even the coffee shops have a chic vibe, replacing dishes like stale bagels and cream cheese with tempting ingredients like smoked salmon served on eggs benedict or avocado toast courtesy of Espresso 21.
Unionville institutions include burgers and beer on the shady backyard patio at good old Jake’s on Main and classic Italian at the very inviting Il Postino. Partake in community festivities at the annual Unionville Festival, a tradition since 1969. The main street creates a pedestrian walkway to indulge in Unionville’s best food, listen to live entertainment, and join in activities. Pause at Toogood Pond to watch the ducks or stroll the south side of the park’s walkway, shaded by a canopy of trees.
Tobermory
At the tip of the Northern Bruce Peninsula sits the tiny town of Tobermory. While the main strip is micro-sized, the seaside feel of the town transports you to a slower pace of life.
The stunning sight of sailboats docked at the marina, unexpectedly green-blue waters, and tiny shops and motels overlooking the harbor has a wistful feel. While not technically a “strip,” the main street wraps around Little Tub Harbour like a warm hug.
Despite its tiny size, Tobermory is more than capable of delivering satisfying meals, including golden fried fish and chips made to order at town landmark Shipwreck Lee’s. Known for their fresh white fish and all-you-can-eat fish and chips, guests never leave hungry.
Tobermory Brewing Co. & Grill’s little red clapboard house creates a quaint picture on the main strip. It offers exceptional views of the harbor as a pleasant spot to sample their craft beers. They also have an eclectic menu and beer shop.
The town’s intriguing maritime history draws visitors to one of Canada’s most unusual national parks, Fathom Five. Visitors can explore the ruins of shipwrecks via glass-bottomed boats. Wrecked in 1885, the Sweepstakes is a popular attraction visible under just 20 feet of water. Scuba divers can also explore the underwater marine museum. Tour boats also venture out to Flowerpot Island to view the unusual rock formations, while the mighty Chi-Cheemaun ferries passengers to the shores of Manitoulin Island and offers peaceful views of Georgian Bay.
Elora
Elora is a historic mill town on the Grand River in Wellington County. The Old Mill dominates the town, with its intricate stone façade poised on the edge of the Elora Gorge beside a cascading waterfall. The surrounding limestone buildings at the mill give Elora a very distinct look, with European influences. An impressive mix of quaint brick, stucco, and clapboard façades avoids the typical look of ho-hum small towns.
The ELORA MEWS is a cloistered courtyard featuring eight shops. Sheltered by centuries-old stone walls and accented by lanterns, the shops sit beside a footbridge overlooking the Grand River. Avid readers can scour shelves of used books at Cordial Clove Books Inc., where owners make you feel like you are borrowing a book from old friends. Epiphany Apparel has a chic, old-world vibe, boasting unique fashion finds.
Fromagerie Evelyn and Elora Bread Trading Company cater to the discerning foodie with palate-pleasing goods ideal for a picnic at Elora’s Bissel Park. For home décor DIYers, Mermaid In Elora offers a collection of vintage and heritage “final touches” that create standout spaces.
Epicurious experiences range from authentic French crepes at Café Creperie to afternoon tea at The Wild Tart. Casual dining at The Friendly Society has a slightly elevated feel that is still warm and cozy, while The Evelyn’s French-inspired menu includes vegan delights.
Niagara-on-the-Lake
Niagara-on-the-Lake’s broad boulevard features perfectly manicured gardens that change with the seasons. The brick Memorial Clock Tower sits watch over the town’s charming historic buildings, located in the heart of Niagara wine country.
A short drive from the majestic Niagara Falls, Niagara-on-the-Lake serves as a rest stop for tourists looking for a more sophisticated regional experience. The 19th-century village is rooted in Canadian history, including the War of 1812's Fort George.
The Victorian architecture of the Prince of Wales Hotel includes a corner entrance, a charming front porch, arched windows, and intricate detailing on the second-floor windows. The hotel wraps around a hidden, tranquil fountain, and each area reveals stunning details, from library shelves to fireplaces and gilt-framed paintings down elegant halls.
Photo bugs clamor to get shots of the Niagara Apothecary and colorful red and green clapboard Just Christmas store. A stop at the original Canadian icon, Greaves Jams, Jellies, and Marmalades, elevates your breakfasts with sweet, fruity spreads.
For the full Niagara-on-the-Lake experience, grab a table at The 11th Post. Two Sisters Vineyards is the genius behind the original dishes and Niagara region wines served in this charming clapboard house.
Midland
Midland is a must-see stop when exploring the Georgian Bay area of Simcoe County. The downtown strip creates a captivating picture with views of Midland Harbour. Many downtown edifices sport colorful murals depicting the area's history. You can stroll the side streets to see all 33 murals!
To sample a true Canadian/Ontario treat, visit Midland during the award-winning Ontario’s Best Butter Tart Festival. This sweet, gooey tart is similar to pecan pie but often features raisins and walnuts. In honor of this Canadian classic, the vibrant main street becomes an open marketplace. Dillon’s Wood Fired Pizza ruins ordering pizza from your local joint. Reservations are a must if you want to sample these stellar pies. Frankly Speaking is a unique twist on the American speakeasies, made notorious during Prohibition. A mix of vintage and signature cocktails and small plates is an entertaining way to spend the evening.
Main strip home décor shopping leans into the rustic charm of cottage country with a sophisticated twist at Cabin Boy and Simply Country. Although not on the main strip, you can experience the different elements of local history. Sainte-Marie-Among-the-Hurons recreates the lives of missionaries and Huron-Wendat people in a reconstructed 1639 fort. Discovery Bay is a colonial site featuring a reconstructed naval/military base and historic vessels, the H.M.S. Tecumseth and the H.M.S. Bee.
Port Perry
Port Perry is located on the shores of Lake Scugog in the Durham region. The downtown strip offers a unique shopping experience and the chance to sample creative menus offered by local chefs. With the small lake visible as you stroll the streets, the town has a very serene feel, even when bustling with summer tourists.
Breakfast aficionados line up to get their Saturday morning fill of Hank's Pastries' pancakes, waffles, bacon, eggs, and French toast. The breakfast line competes with bakery customers waiting to place their orders for an impressive list of mouthwatering breads, savory pastries, and sweet treats, including their trademark “big as your face” apple fritters and butter tart donuts.
New to the Port Perry strip, The Port Social is a small local eatery already making a name for itself for its comfy dining area, vibing music, and something-for-everyone menu. Venture off the main street to sample craft beers at Old Flame. Located in the former firehouse, it has a pleasant back porch in the summer, live local music, and a friendly atmosphere.
Uxbridge
Known as the Trail Capital of Canada, Uxbridge is another Durham region find. The main strip has a boulevard feel with angled parking, which also makes it easier to access the local shops and eateries.
The Uxbridge wrought iron clock outside Rutledge Jewellers is a recent addition, yet it adds a quaint feel to the main strip. Built by historic clockmakers, the Verdin Clock Company, which has been operating since 1842, gives the clock its authentic heritage feel.
Vintage movie theater, The Roxy’s pale blue façade is a town landmark. It is also a community hub known for art film events, fundraisers, and annual short film festivals in September and October.
Browse the high-end clothing boutiques, including Threads, Jillian’s, and Woods, or discover the perfect gift at Presents Presents Presents and The Lemonade Stand. Find upscale skin care products at House of T•L’s modern apothecary or indulge in gourmet delights at DesBarres Chocolate and Gratton’s Greatest for small-batch finds.
The Uxbridge Heritage Train Station and the Uxbridge Public Library, with their unmistakable Victorian Gothic architecture and impressive clock tower, are worth a few selfies. Summer visitors, be sure to check out the beer garden at the Second Wedge Brewery. Sample craft beers and ciders and gobble down Foundry Pi’s wood-oven pizza made in a quirky blue shipping container.
Port Stanley
On the shores of Lake Erie, Port Stanley’s beaches offer heart-pounding entertainment watching the daring skills of parasailers. A tiny town with epic-sized adventures, Port Stanley is quintessentially beachy.
The blue clapboard Kettle Creek Inn is a familiar sight in Port Stanley, creating a warm welcome as you arrive in town. Its cozy front porch, quaint gardens, intimate dining experiences, and well-appointed rooms offer comfy accommodation if you plan to stay the night.
Its sweeping main strip gives strollers room to breathe compared to typical Ontario small towns with tightly knit row-style buildings. Instead, sweet little spots like The Harbour Merchant Coffee Company and Main Street Taqueria sit nestled among open views of the water and charming homes. Both excel at what they do, with the taqueria’s authentic Mexican and the coffee company’s small-batch roasts.
Owned and operated by area artists, The Art Emporium houses an intriguing collection of local works. However, the town is all about its icons, including creamy sweet treats at Broderick’s Ice Cream Parlor. Dining at The Buccaneer Bar & Grill is another town tradition, with a patio right on the beach. If you love the theater, attend the Port Stanley Festival Theatre Simon Joynes Playwrights’ Festival in September to discover the work of up-and-coming playwrights.
With so many small towns to explore, it is no surprise the province’s slogan is “Yours to Discover.” Whether you want a short drive from Ontario’s cities or a leisurely weekend road trip, the prettiest downtown strips in Ontario make the journey worthwhile, all the while offering plenty of natural scenery one's heart could desire.
