11 Best Lakeside Towns in The Great Lakes
The Great Lakes region packs an enormous range of standout experiences into one freshwater corridor, from Lake Superior lookouts and Lake Michigan beaches to Georgian Bay shipwreck tours. In Niagara-on-the-Lake, the biggest draw is the rare setting at the point where Lake Ontario meets the Niagara River, paired with easy access to more than 100 wineries in the surrounding Niagara Wine Country. For a US destination, on Mackinac Island, you can explore a car-free community by horse-drawn carriage or bicycle between Lake Huron and Lake Michigan, then stop for the town’s famous fudge. There's so much to see and do around the Great Lakes, so here are 11 of the best small towns to visit for the best lakeside experiences.
Niagara-on-the-Lake, Ontario

Niagara Falls is a beautiful city on the water, but it can’t match the sense of community found in Niagara-on-the-Lake, Ontario, Canada. This historic town is filled with Victorian architecture, local cafes, and things to do. The town sits on the southwest shore of Lake Ontario, where the lake meets the Niagara River, near the US border.
The town is home to several War of 1812 military sites alongside its famous Shaw Festival, a theater festival known for beautiful venues and fantastic talent. Wine lovers will also love Niagara-on-the-Lake for its position in the heart of Niagara Wine County. There are over 100 wineries in the area to visit and several bars in town serving local varieties.
Mackinac Island, Michigan

Mackinac Island, Michigan, sits between two of the Great Lakes, Lake Huron and Lake Michigan, sitting at the intersection of that state’s Upper and Lower Peninsulas. The town has been car-free since the turn of the 20th century (well over 100 years) and embraces a slower pace of life, one traversed largely on foot or by bicycle (or even horse-drawn carriage).
The town’s architecture has a distinctly Victorian aesthetic while still embracing the comforts of modern life. Visitors can explore the island with one of its famous horse-drawn carriage tours or rent a bike and pedal to one of its local museums. The town is also world-famous for its Mackinac Island Fudge, so be sure to grab a sweet bite to eat while you’re there.
Tobermory, Ontario

Tobermory, Ontario, Canada, was built on the backside of the Niagara Escarpment and is surrounded by Lake Huron and Georgian Bay. Visitors to town can stop by Little Tub Harbour for a stroll by the water or to grab a bite at one of the many fish and chips restaurants. While in town, hop on board a glass-bottom boat tour and see the Great Lakes up close and two shipwrecks to boot.
The Niagara Escarpment is also a UNESCO Biosphere Reserve, giving the area ample hiking opportunities for nature lovers, including one end of the Bruce Trail, a 559-mile (or 900-km) trail. In addition to the Niagara Escarpment, Tobermory also acts as the entry point to two Canadian National Parks, including Bruce Peninsula National Park and Fathom Five National Marine Park.
Grand Marais, Minnesota

Grand Marais, Minnesota, is home to the state’s longest-running art colony and lies on Lake Superior's northwestern shore. Visitors can explore Artist's Point, a geological anomaly that sits between East Bay and Grand Marais Harbor. This area gives explorers the perfect place to view the lake. Art lovers can also take part in one of the regular workshops put on by the Grand Marais Art Colony.
The lake isn’t the only nature to take in while visiting Grand Marais. The area is also home to the densely forested Sawtooth Mountains. Visitors can explore the boreal forests, hike, or ski the trails at Pincushion Mountain.
Holland, Michigan

Holland, Michigan, is a beach town with a hint of European zeal. The Dutch heritage of the town can be seen in its brick buildings and the flower beds that line its streets. Visitors can also shop for quintessential Dutch items while in town, like wooden clogs, traditional sweets, and cold pilsner beer.
Locals can enjoy the semi-weekly farmers market along the west end of 8th Street and access to the Windmill Island Gardens just across the Macatawa River. These gardens provide yet another taste of the Netherlands and boast a Tulip Time Festival each spring.
If you’re looking for some time at the beach, you can also visit Holland State Park. While there, rent a cabin or RV to get the full experience, and be sure to check out "Big Red," the town’s lighthouse.
Collingwood, Ontario

Collingwood, Ontario, Canada, sits on Nottawasaga Bay (a sub-bay of the Georgian Bay) and boasts year-round activities. In the winter, the town’s famous Blue Mountain ski resort is perfect for a day in the snow, and in the summer, visitors can take the gondola up the mountain and mountain bike or hike their way down.
Check out the local Collingwood Farmers’ Market, take a ride on the Ridge Runner mountain coaster, or head to Collingwood Harbour to canoe, kayak, and paddleboard. Sunset Point is also a great waterfront park for an afternoon stroll.
South Haven, Michigan

South Haven, Michigan, sits upon Lake Michigan's southwestern shoreline. Wide beaches sit on either side of the Black River, giving the area a ton of waterfront space. The town is also home to a walkable pier, complete with a red lighthouse. The South Beach is family-friendly with parks and playgrounds, while the North Beach across the way is better for those looking to enjoy ample concession stands and summertime indulgences.
Old Harbor Village is also a great place to stop in if you’re looking to shop. This area is home to several bars and boutique shops that fit perfectly into the timeless New England feel of the neighborhood. There is also the Michigan Maritime Museum for history lovers, which boasts a complete working replica of the Friends Good Will, an 1810s topsail sloop.
Owen Sound, Ontario

Owen Sound, Ontario, Canada, is a small city located on the southern shores of Georgian Bay. The town has a fantastic blend of nature and culture, giving visitors the true Canadian experience. Check out the Inglis Falls Conservation Area for an afternoon of hiking surrounded by ferns, trees, and waterfalls. The area is also home to Jones Falls and Indian Falls if you’re looking for a full day of nature.
The town is also home to several local art galleries and museums, including the Tom Thomson Art Gallery and the Billy Bishop Home Museum and National Historic Site. Smaller galleries in the area include the Gallery de Boer Fine Art and the Owen Sound Artists' Co-op.
Harbor Springs, Michigan

Harbor Springs, Michigan, was once revered by the Ojibwe for its mineral springs. Today, the town on Lake Michigan provides locals and visitors with the perfect balance of small-town charm and outdoor adventure. Check out the Harbor Springs Lyric Theatre, a nonprofit movie theater offering first-run, classic, and family-favorite movies right on Main Street, or drive the famous Tunnel of Trees Scenic Heritage Route. Nature lovers can also visit the Thorne Swift Nature Preserve. History lovers, on the other hand, might like to spend an afternoon at the Andrew J. Blackbird Museum.
Pelee Island, Ontario

Pelee Island, Ontario, is the southernmost inhabited point in Canada. The Township of Pelee on Pelee Island sits in Lake Erie and welcomes one of Canada's most mild climates. The island is also home to two wineries, including Pelee Island Winery, Canada’s southernmost estate winery.
Visitors can also enjoy exploring the island by taking a stroll, swimming on one of the island's many beaches, or hopping on a bike. True lovers of nature can also check out the Pelee Island Bird Observatory, a special area for bird watchers, as it sits in the path of two major songbird migratory flyways. These birds winter in Central and South America but fly north in warmer weather to breed in Ontario.
Westfield, New York

Westfield, New York, sits on Lake Erie, with Chautauqua Creek running through the town’s center. The town is home to lush vineyards and the rolling hills of upstate New York, with the lake giving the town a serene feel. Visitors can enjoy the local beaches and harbor or head into town to check out the local shops and cultural sites.
While visiting, there are also plenty of opportunities for fishing, sailing, golfing, and even skiing in the colder months. For wine lovers, Westfield is in the heart of the world’s largest Concord Grape Belt, and most of the local wineries offer year-round tastings.
Lakeside Living and Outdoor Adventures
The Great Lakes Region is home to countless lakeside towns. These destinations are perfect for quiet weekend getaways filled with outdoor activities, art galleries, and local cafes. Spanning from Ontario, Canada, to Michigan, Minnesota, and New York, these towns each offer something different to visitors looking to spend some time on the water in one of the most geographically interesting regions in North America. From hiking trails to local wineries, the Great Lakes Region has countless activities to offer people of all ages and backgrounds.