One of the best things about living in Oakville is how perfectly placed it is. Nestled between the shores of Lake Ontario and major highways, Oakville residents have easy access to some of Southern Ontario’s most beautiful and exciting day-trip destinations.
Whether you’re craving a charming small town, a nature escape, or a wine-tasting afternoon, these 10 day trips from Oakville are perfect for couples, families, or solo explorers.
1. NIAGARA-ON-THE-LAKE
Approx. 1 hr 15 min drive
Step into one of Ontario’s most picturesque and historic towns. Niagara-on-the-Lake is a dream day trip for wine lovers, foodies, and anyone craving small-town charm. Meander through the flower-lined Queen Street filled with boutique shops, cozy cafés, and old-world architecture. Be sure to visit a few of the region’s top wineries like Peller Estates or Trius for tastings with vineyard views. You can even add a stop at Fort George or stroll along the waterfront for a full afternoon escape.
2. ELORA & ELORA GORGE
Approx. 1 hr 20 min drive
Elora blends outdoor adventure with artistic flair. Its dramatic limestone cliffs and rushing river make Elora Gorge Conservation Area a go-to for hiking, tubing, or even cliffside picnics. The nearby Elora Quarry is perfect for a summer swim surrounded by towering rock walls. After your outdoor adventure, head into town for local art galleries, craft shops, and historic buildings — all wrapped up in that signature small-town Ontario charm.
3. STRATFORD
Approx. 1 hr 30 min drive
Stratford is a haven for theatre lovers and culture seekers alike. Home to the renowned Stratford Festival, it draws visitors from around the world — but the experience doesn’t stop at the stage. Wander through quaint streets dotted with local restaurants, artisan shops, and tranquil green spaces along the Avon River. It’s also a great spot to enjoy a picnic, people-watch, or even take a scenic paddleboat ride. And yes — Bieber fans, you’ll find a few spots tied to his early days!
4. PRINCE EDWARD COUNTY
Approx. 2 hr 45 min drive
Though it’s the furthest on this list, Prince Edward County is absolutely worth the drive. Known for its world-class wineries, art galleries, and rural elegance, PEC offers the ultimate wine-country day trip. Explore the sandy dunes at Sandbanks Provincial Park, enjoy a tasting flight at Huff Estates or Grange of Prince Edward, and pop into the charming towns of Bloomfield or Picton for boutique shopping and fresh farm-to-table eats. Go early — you’ll want every minute!
5. ROYAL BOTANICAL GARDENS (BURLINGTON)
Approx. 25 min drive
Just a quick hop from Oakville, the RBG is perfect for families, plant lovers, or anyone who enjoys a peaceful outdoor stroll. It’s one of the largest botanical gardens in Canada, featuring themed gardens, nature trails, and seasonal exhibits. In spring and summer, expect bursts of colour from tulips, lilacs, and roses. The trails that wind through forested areas and marshland also make it a great nature escape — without the long drive.
6. PORT CREDIT
Approx. 20 min drive
This lakeside village within Mississauga feels like a mini escape without leaving the GTA. Port Credit’s walkable waterfront is filled with marinas, seafood restaurants, ice cream parlours, and patios with a view. Whether you’re enjoying fish and chips by the lighthouse or paddleboarding on the lake, it’s a quick and scenic getaway perfect for a sunny afternoon or sunset date.
7. ST. JACOBS VILLAGE & FARMERS’ MARKET
Approx. 1 hr 15 min drive
Step back in time and into one of Ontario’s most unique rural communities. St. Jacobs is known for its Mennonite heritage, artisanal culture, and Ontario’s largest year-round farmers’ market. Start with warm pastries, handmade cheese, and local crafts at the bustling market. Then take a stroll through the village for quaint storefronts, museums, and horse-drawn buggy sightings. It’s a wholesome, feel-good experience for all ages.
8. RATTLESNAKE POINT & CRAWFORD LAKE
Approx. 35–40 min drive
Outdoor lovers will feel right at home here. Rattlesnake Point offers cliff-edge hiking trails with panoramic views of the Niagara Escarpment. It’s especially stunning in fall when the leaves change. Just minutes away, Crawford Lake adds another layer of interest with a peaceful boardwalk, a rare meromictic lake (where the water layers don’t mix!), and a reconstructed Indigenous longhouse exhibit. This duo makes for a nature-packed, educational, and active day out.
9. HAMILTON WATERFALLS TOUR
Approx. 45 min drive
Hamilton isn’t just steel and factories — it’s also the waterfall capital of Ontario. With over 100 falls in the area, you can easily make your own scenic tour. Start with Webster’s Falls, Albion Falls, and Tiffany Falls for dramatic backdrops and photo ops. Add in a forest hike or stop in nearby Dundas for a cozy lunch. Great for couples, families, or solo explorers who want a blend of activity and awe.
10. BLUE MOUNTAIN VILLAGE
Approx. 1 hr 45 min drive
This popular ski town is also packed with things to do in the warmer months. Blue Mountain Village has gondola rides with sweeping views, ziplining adventures, mountain biking trails, and a selection of stylish restaurants and shops. You can also unwind at Scandinave Spa nearby for some hot-cold therapy surrounded by nature. Whether you're feeling active or in full relaxation mode, it’s a full-day escape that never disappoints.
Why It Matters
One of the perks of living in Oakville is being surrounded by so many unique getaways. Whether you're entertaining guests or just need a change of scenery, these trips are a reminder that the GTA is more than just traffic — it’s full of hidden gems.
At Lakeshore Group Real Estate, we know Oakville is more than just a place to live — it’s a lifestyle worth exploring.
Thinking of making Oakville your home base for adventure?
Let’s chat about finding a home that fits your lifestyle — lakeside, family-friendly, or low-maintenance luxury.
📞 Contact us today or follow us on Instagram @lakeshoregroupre for more local tips and listings!