Quaint & charming small towns in Ontario

Niagara-on-the-Lake

Drive for 25 minutes north from Niagara Falls, and you’ll find Niagara-on-the-Lake: a small, historic town in the heart of Niagara’s wine country. Niagara-on-the-Lake’s cobblestone streets and British Classical buildings, which earned the town its designation as a National Historic Site, will make you feel like you’ve stepped back into the early 19th century. With a wealth of beautiful shops and well-established wineries populating the area, it’s the ideal place for a romantic trip with your partner.

What to do

Take a stroll through Niagara-on-the-Lake’s renowned heritage district and learn about the area’s interesting history with informative plaques and beautiful British classical architecture along the popular Queen Street. Between April and December, catch your favourite play at the Shaw Festival. A range of plays inspired by famous playwright George Bernard Shaw are sure to entertain you with top-notch singing and dancing from beginning to end.  

Niagara-on-the-Lake is home to North America’s oldest golf course, the Niagara-on-the-Lake Golf Club.  Book a tee time and admire the views of Lake Ontario

Once an important military fortification during the War of 1812, the Fort George National Historic Site is now a cultural attraction located along the Niagara River. Learn more about the history and operations behind this important spot by signing up for a private tour with a knowledgeable guide, complete with a musket demonstration.

As Niagara-on-the-Lake is famous for its outstanding wine, over 40 wineries can be found around the area. Some recommended places for Niagara-on-the-Lake wine tours are Wayne Gretzky Estates, Peller Estates, Jackson-Triggs Winery, Inniskillin Winery, Konzelmann Estate Winery, Two Sisters Vineyards, Strewn Winery and Reif Estate Winery.

Insider Tip: Icewine is a popular dessert wine that’s made from grapes that are frozen while still on the vine. Known for its rich sweetness and high acidity, Canadian icewine was first introduced to the public market from Inniskillin Winery in Niagara-on-the-Lake. One of the best places to try icewine is in Peller Estates’ 10Below Icewine Lounge, kept at a chilly -10°C—the best temperature for harvesting icewine grapes. If you’re not dressed for the cold weather, don’t worry—Peller Estates supplies wine tasters with warm Canada Goose parkas and gloves.

Where to eat

• Treadwell Cuisine: This upscale Canadian restaurant features a seasonal menu paired with regional wines. If the weather is nice, enjoy your meal on the outdoor patio. 
• Tiara Restaurant: Enjoy the view of the Niagara River while dining on scrumptious international cuisine made with locally sourced ingredients.

Where to stay

• Vintage Inns: Enjoy luxury amenities and quality hospitality at vintage inns across Niagara-on-the-Lake such as Pillar & Post, Prince of Wales Hotel and Queen’s Landing.
• Oban Inn: This significant heritage hotel is a close walk from the Shaw Festival theatres and Queen Street shopping scene. 
• 124 on Queen Niagara-on-the-Lake: Luxurious accommodations, an outstanding spa and a delicious restaurant can be found in this historic hotel in the heart of Niagara-on-the-Lake’s famous Old Town.  
• Charles Inn: Admire the elegant architecture and enjoy pampered service at this luxurious hotel. 
• Shaw Club: One of the best Niagara-on-the-Lake hotels, this intimate retreat is steps away from the top culture and leisure spots in town.

Huntsville

In the heart of the Muskoka region, on the forested terrain of the Canadian Shield, lies the town of Huntsville. There’s no better place to go if you’re looking to visit all the best spots in Muskoka. A three-hour drive from Toronto, Huntsville is the largest community in the region and close to signature spots like Algonquin Park and Arrowhead Park. Here, you can enjoy outdoor activities like paddling, hiking, and cycling, as well as exploring the history and culture of the town.

What to do

Witness Huntsville’s best outdoor spots by visiting wilderness havens like Lions Lookout and Limberlost Forest & Wildlife Reserve. In addition to admiring the beautiful scenery, you’ll be able to enjoy hiking, cycling, canoeing, disc golf and more. 

Dog sledding is one of Huntsville’s most exciting winter sports. If you’re visiting during the snowy season, make sure you visit North Ridge Ranch. Bond with their energetic pack of Alaskan huskies before heading on an unforgettable ride through pristine snow.  

Take in Huntsville’s diverse local arts and culture scene. Muskoka Heritage Place is home to many historical relics such as the Portage Flyer Train, Rotary Village Station and the Muskoka Pioneer Village. Art lovers will delight in seeing the Group of Seven Murals, an amazing collection of over 90 murals located at various points around town. And don’t forget to stop by Sugarbush Hill Maple Farm and see how maple syrup is made—it’s an important part of your Canadian trip.

Where to eat

• Muskoka Roastery Coffee: Stop by in the morning for a cup of hot, delicious coffee.
• Farmer’s Daughter: This grocery store offers fresh produce, homemade baked goods, deli meat and other local foods, as well as seasonal specialities like holiday gift baskets. 
• Huntsville Brewhouse or Muskoka Craft Brewery Tours: Unwind after a long day of outdoor fun with delicious drinks.

Where to stay

• Deerhurst Resort: A fun-filled, year-round activity resort, perfect for outdoor enthusiasts. 
• Trillium Resort & Spa: Bask in this relaxed, peaceful resort tucked away in forested woodlands. 
• Jaynes’ Luxury Cottages: Offers luxury cottage rentals with concierge services to meet your every need. 

Insider Tip: Huntsville isn’t the only wonderful place in the region. Consider also checking out the other great Muskoka towns such as Bracebridge, Bala, Port Carling and Gravenhurst for more exciting adventures in this region.

Stratford

With a vibrant theatre and festival scene, 19th century architecture and picturesque outdoor gardens, Stratford is a lovely place to visit during any time of year.  The hometown of Justin Bieber, this quaint town is also recognized for the Stratford Festival and its bustling downtown populated with fantastic shops and restaurants. It’s a great addition to any Ontario trip, as the town is located just two hours and a half west of Toronto.

What to do

The Stratford Festival is one of the most famous repertory theatres in Canada, running from April to October. With four permanent venues in the town and a wide selection of world-class plays, it draws theatre enthusiasts from all over the world.   There’s even a Stratford Direct bus from downtown Toronto to the theatres. 

Insider Tip: If you have your heart set on watching a specific play, book your tickets early to avoid disappointment. Alternatively, check the website often for possible discounts and deals on your next night at the theatre. 

Stratford also has some beautiful outdoor spots and historic attractions. You can’t visit the town known for its Shakespeare plays and not pay a visit to the Shakespearean Gardens, where you’ll find a bust of the playwright among the beautiful plants. The late 19th century building of Stratford City Hall was designated a National Historic Site of Canada for its regal appearance that blends a variety of architectural styles from the late Victorian era. 

Where to eat

• Stratford Chocolate Trail Burns & Calories: Sweet lovers will enjoy this self-guided tour that takes you through world-famous confectioners and bakers across the town. Pick your top six stops and redeem your vouchers at the corresponding locations for sweet deals on quality chocolate. 
• Braai House: With its location right behind Avon Theatre, paired with its African-inspired menu of mouthwatering pizzas, steaks and other barbecued dishes, it’s no wonder this restaurant is a top pick for both locals and tourists.
• Pazzo Pizzeria: Order Stratford’s tastiest classic or customizable thin crust pizzas to share with your partner or group of friends.

Where to stay

• The Bruce Hotel: This elegant hotel is close to the Stratford Festival and many delicious cafés and restaurants, including the on-site ‘The Restaurant at the Bruce’. 
• The Parlour Inn: Luxurious comfort and a warm, welcoming atmosphere await you at this landmark historic hotel in downtown Stratford. 
• Hughson Hall: Enjoy spacious rooms, attentive service and delicious meals at this Victorian-style bed and breakfast.

St. Jacobs

Two hours west of Toronto is St. Jacobs, a charming community brimming with history and culture. A favourite destination for history buffs as well as culinary lovers, the town is steeped in Mennonite culture and famous for its lively seasonal events.

What to do

For boutique shopping, the Village of St. Jacobs is located downtown, near the Conestoga River. With a variety of local merchants featuring specialty shops, arts and culture stands, food and drink shops and more, it’s easy to spend an entire day in this historic shopping district. You can also do some outlet shopping on the edge of town at St. Jacobs Outlets.

Learn more about Mennonite culture at the Mennonite Story Interpretive Centre, which offers guided tours through interactive displays and video presentations.

Where to eat

• St. Jacobs Farmers’ Market: As Canada’s largest year-round market, the St. Jacobs Market in Ontario features over 250 vendors with fresh local produce, quality meats and cheeses, international cuisine, homemade jewellery and more. 
• Crowsfoot Smokehaus: This popular German-style barbecue grill also has an on-site general store stocked with artisanal products, fresh produce and everyday essentials.
• Stone Crock Bakery: You’ll find artisanal fruit pies, breads, scones, muffins and other scrumptious pastries at this Mennonite-run bakery.

Where to stay

• Explore Hotels, Motels & Inns in the Waterloo Region to find incredible hotels in and around St. Jacobs.

Elora

Explore unique boutiques, awe-inspiring galleries and colourful artists’ studios in Elora, Ontario. This quaint small town, located two hours west of Toronto, has plenty of gorgeous natural scenery and exciting cultural festivals that people of all ages will love.

What to do

There’s never a bad time to visit Elora, because events take place in this bustling town all year long. The Elora Festival is Canada’s international choral festival, with internationally acclaimed choirs and vocal ensembles performing over three weeks every July. Enjoy a full weekend of arts, music, food and culture at Riverfest Elora, which takes place in the beautiful Bissell Park along the Grand River. 

Make sure to visit the Elora Gorge Conservation Area and witness the Grand River flowing past 22-metre high cliffs. Scenic overlooks with safety barriers allow you to get a close up view of this spectacular natural attraction in the Grand River Valley. It’s also a great spot for outdoor activities like tubing, canoeing and hiking. The Elora Quarry, encircled by 12-metre high cliffs, is another popular spot for swimming and picnicking.  For more adventurous pursuits, check out Grand River Outfitting and Fly Shop for guide services that will advise you on the best local fishing spots on the Grand River.  

There’s also great scenic spots like the West Montrose Covered Bridge, which spans the Grand River. One of the oldest covered bridges in Canada and the last of its kind in Ontario, it became known as the “Kissing Bridge” because of the toll—a private kiss—that was once required to cross it.

Where to eat

• Elora Bread Trading Company: Sample traditional, naturally leavened baked bread and goodies at this artisanal bakery.
• Elora Brewing Co.: Set inside a historic limestone building, you’ll find great beer, food and music at Elora’s prime late-night hangout. 
• Elora Mill Restaurant: This two-story restaurant highlights produce from its local, organic farm with creative, delicious dishes. 
• The Evelyn: With a relaxed atmosphere, outdoor patio and French-inspired entrées, there’s no better place to enjoy a casual family lunch or delightful romantic date. 

Where to stay

• Elora Mill Hotel & Spa: Perfect for those looking for a rejuvenating spa treatment and fine dining experience.

Picton

Picton, Ontario is a charming small town at the heart of beautiful Prince Edward County. Located three hours east of Toronto and an hour west of Kingston, this up-and-coming hotspot for visitors is widely recognized for its variety of distinctive hotels, delicious local restaurants and diverse small businesses.  Use Picton as your base for exploring Prince Edward County (PEC), which has plenty of exciting activities for you to participate in during your stay.

What to do

PEC has a rich agricultural history and today it’s home to over 35 distinctive wineries, as well as craft breweries, cideries and distilleries. Sample your way along the Taste Trail, which also includes some of the county’s best farm-to-table eateries and farm stands. Some iconic places are Hinterland Wine Company for delicious sparkling wines, Waupoos Estates Winery for their lakeside wine and cider and Closson Chase Vineyards for their fruity Pinot Noir. 

Discover artisanal cheese at Fifth Town, which uses cow milk from local farms like Jean’s Quinte Crest just down the road. You can try the cheeseboard grazing boxes on their outdoor patio bar, or take some to enjoy at your hotel. 

Music lovers will want to hit up the Prince Edward County Jazz Festival, an annual event that draws visitors to Prince Edward County from all over the world. Held in mid-August, it brings together the top jazz musicians to perform over 30 concerts for fans.

Where to eat

• Bocado: Spanish-inspired cuisine, cocktails and wines are bestsellers on the menu. 
• The Miller House at Lake on the Mountain: Stunning outdoor views and sharing platters made with local ingredients—there’s no better way to enjoy your summer getaway.

Where to stay

• The Royal Hotel: This charming hotel is situated in the heart of Picton, steps away from its most popular restaurants.. 
• The June Motel: Enjoy the retro vibes of this hip, boutique motel with beautiful views of the bay. 
• Merrill House: Fine dining and luxury accommodations combine in this Victorian era hotel. 
• The Waring House: Brush up on your cooking skills by taking a class from experienced chefs at this historic country inn. 
• Picton Harbour Inn: Located on the north side of town, this hotel offers fantastic views of Picton Harbour.

Insider Tip: Accommodations for Prince Edward County fill up fast, especially in the summer. If you’re planning a trip here, book as early as possible!

Kingston

Historic architecture, contemporary attractions and a lively downtown shopping scene are just a few of the things that the small city of Kingston is known for. As the former capital of Canada, and its location just a two hour drive from Ottawa, it’s the ideal destination for your next romantic getaway or fun-filled family vacation.

What to do

The Kingston Public Market is the oldest farmers’ market in the province, with origins dating back to 1801. Located in downtown Kingston, Ontario, behind the City Hall, it’s open from April to November and features a diverse range of vendors with wares ranging from local produce to handmade arts and crafts. 

Explore the Fort Henry National Historic Site during the spring and summer season. Formerly a major trans-shipment point during the 19th century, visitors can learn about historical military life on guided tours and watch military demonstrations by the Fort Henry Guard. 

If you’re a fan of spooky stories and all things supernatural, Kingston’s Haunted Walk Ghost Tours is chillingly perfect for you. You’ll be led through the city’s haunted hotels, hidden burial grounds and the site of grave robbings. 

Do you love art? In the Agnes Etherington Art Centre, you’ll find the largest authenticated collection of Rembrandt paintings in Canada—four of them. In addition to these masterpieces, this free, year-round gallery displays 2,500 objects from the 14th to the 20th century, including Dutch and Flemish art from the Baroque era. 

Insider Tip: Need help finding the best places to visit in Kingston? Kingston Trolley Tours offers guided tours through the city’s historic old town and downtown shopping district, with detailed stops at iconic visitor attractions, museums, art galleries and historic sites. 

Where to eat

• Tango Nuevo: Enjoy cosmopolitan wines and dishes made with locally sourced ingredients in this tapas & wine bar. 
• Kingston Food Tours: The perfect way to explore the best local restaurants while learning about the city’s culture and history from your knowledgeable guide.

Where to stay

• Historic Inns and B&Bs in Kingston: Some top picks are Rosemount Inn, Hochelaga Inn, All Suites, Whitney Manor and the Frontenac Club Inn
• Delta Hotels Kingston Waterfront: This amazing hotel is situated in downtown Kingston, with picturesque views of the Confederation Harbour and Lake Ontario.

Rideau Heritage Route

A UNESCO World Heritage Site, the Rideau Heritage Route is a scenic tour route between Kingston and Ottawa that takes you through the local locks and mills of the Rideau Canal. Whether you’d like to cruise along the Rideau Canal by boat or travel along the winding roads past every small town, you’ll enjoy the picturesque nature, fascinating history and outdoor adventure on your journey. 

What to do

During your exciting adventure along the Rideau Heritage Route, you’ll pass through numerous charming small towns such as Elgin, Smiths Falls, Manotick, Westport and Merrickville, Ontario. Many are home to lock stations, which allow anyone travelling by boat to pass through waters with differing sea levels. In these towns, you’ll also have the opportunity to see quaint village shops, historical buildings and other scenic attractions. Some popular spots include the Rideau District Museum in Westport, the Stone Arch Dam in Elgin, Stewart Park in Perth, Frontenac Provincial Park in Sydenham, and the haunted Watson’s Mill & Dickinson House in Manotick.

Where to eat

• The Opinicon: Open during the spring and summer, you’ll enjoy delicious seasonally inspired cuisine made with local ingredients at this modern retreat.
• The Cove: This year-round restaurant serves up locally-inspired food in vintage décor and a relaxed atmosphere. As a bonus, you can dine while listening to live music during the summer months. 

Where to stay

• Le Boat: Perfect for those looking for a unique adventure, Le Boat lets you rent a canal houseboat for multiple days and travel wherever you want, whenever you want.  No experience necessary!
• Perth Parkside Inn & Spa: Enjoy stunning waterfront views, complimentary breakfasts and relaxing spa treatments at this cozy hotel.

Insider Tip: Since Ottawa and Kingston are so close by, you can easily turn your visit along the Rideau Heritage Route into a day trip from these cities.

Want to learn more about these small towns in Canada, plus other exciting destinations across the province of Ontario?