How to Spend a Perfect Weekend in Oakville: Activities and Itinerary

Oakville, Ontario, is a gem nestled on the shores of Lake Ontario, offering a perfect blend of urban sophistication and natural beauty. With its scenic waterfront, charming downtown, and numerous parks, Oakville is an ideal destination for a weekend getaway. Whether you're a local looking for a staycation or a visitor exploring this vibrant town for the first time, this itinerary will guide you through a perfect weekend in Oakville.

Day 1: Exploring the Heart of Oakville

Morning: Stroll Through Downtown Oakville

Start your weekend with a leisurely stroll through Downtown Oakville. The historic district is a haven for boutique shopping, art galleries, and quaint cafes. Wander along Lakeshore Road, where you’ll find an array of unique shops offering everything from high-end fashion to artisanal goods.

Breakfast Spot: Begin your day with breakfast at The Green Bean, a cozy café known for its organic coffee and freshly baked goods. Their breakfast sandwiches and pastries are a must-try.

Late Morning: Visit the Oakville Museum at Erchless Estate

After breakfast, head to the Oakville Museum at Erchless Estate. This museum is a fascinating glimpse into Oakville’s past, offering exhibits on the town’s history and its role in the Underground Railroad. The estate itself, once the home of Oakville’s founding family, is a beautiful example of 19th-century architecture.

Location: 8 Navy Street, Oakville

Admission: Free, donations appreciated

Highlights: Explore the historic buildings, stroll through the gardens, and learn about Oakville’s rich cultural heritage.

Lunch: Lakeside Dining

For lunch, enjoy a meal with a view at Harbourside Artisan Kitchen. Overlooking the picturesque Oakville Harbour, this restaurant offers a diverse menu with options ranging from fresh seafood to gourmet burgers. Pair your meal with a local craft beer or a glass of wine from their extensive list.

Must-Try: Their seafood platter is a popular choice, featuring a selection of the day’s freshest catches.

Afternoon: Scenic Walk at Lakeside Park

Post-lunch, take a scenic walk at Lakeside Park. This waterfront park is perfect for a leisurely stroll, with trails that offer stunning views of Lake Ontario. The park is also home to the Thomas House, one of Oakville’s oldest preserved buildings.

Activities: Walk along the shoreline, visit the Thomas House, or simply relax on one of the park’s benches and soak in the serene atmosphere.

Evening: Sunset Cruise on Lake Ontario

End your first day with a memorable experience by taking a sunset cruise on Lake Ontario. Several local companies offer evening cruises departing from Oakville Harbour. This is an excellent way to see the town from a different perspective while enjoying the breathtaking sunset over the water.

Booking: It’s advisable to book in advance, especially during the summer months.

Tip: Bring a light jacket as it can get cool on the water in the evening.

Day 2: Outdoor Adventures and Relaxation

Morning: Bronte Creek Provincial Park

Kick off your second day with some outdoor adventure at Bronte Creek Provincial Park. This park offers a variety of activities for nature enthusiasts, including hiking, bird-watching, and cycling. If you’re traveling with family, the Children’s Farm and playbarn are sure to be a hit with the kids.

Hiking: The park features several trails of varying lengths and difficulties. The Ravine Trail offers a moderate hike with scenic views of Bronte Creek.

Picnic: Pack a picnic breakfast or grab something to-go from a local bakery and enjoy it in one of the park’s designated picnic areas.

Mid-Morning: Kayaking on Sixteen Mile Creek

After exploring Bronte Creek, head to Sixteen Mile Creek for a kayaking adventure. The creek winds its way through the heart of Oakville, offering a peaceful setting for paddling. Rentals are available at Oakville Paddle Sports, and you can choose from kayaks, canoes, or stand-up paddleboards.

Rental Information: Oakville Paddle Sports offers hourly and daily rentals. No experience is necessary, and they provide all the equipment you need.

Route: Paddle towards Lake Ontario for a more challenging route or explore the calmer waters upstream.

Lunch: Farm-to-Table Dining

For lunch, make your way to Seasons Restaurant in downtown Oakville. Known for its farm-to-table philosophy, Seasons offers a menu that changes with the seasons to reflect the freshest local ingredients. The ambiance is upscale yet relaxed, making it a great spot for a leisurely lunch.

Recommendation: Try their seasonal salad or the chef’s special, which showcases the best of what’s currently in season.

Afternoon: Relax at Coronation Park

Spend your afternoon unwinding at Coronation Park. This lakeside park is a local favorite for its beautiful views, sandy beach, and ample green space. It’s the perfect spot to relax after an active morning. If the weather is warm, take a dip in the lake or rent a paddleboard for some fun on the water.

Facilities: The park has picnic areas, a playground for kids, and washrooms.

Tip: Bring a blanket and a good book for a relaxing afternoon on the grass.

Evening: Dinner and Entertainment

For dinner, head to Noble Bistro, an Oakville dining staple known for its creative dishes and elegant atmosphere. Their menu offers a modern twist on classic dishes, with an emphasis on locally sourced ingredients. The cozy ambiance and excellent service make it the perfect place for a special evening out.

Menu Highlight: The duck confit and the chef’s tasting menu are highly recommended.

After dinner, catch a show at the Oakville Centre for the Performing Arts. From live theater and music concerts to comedy shows, there’s always something happening at this cultural hub. Check their schedule in advance to see what’s on during your visit.

Booking: Tickets can be purchased online or at the box office. It’s advisable to book in advance for popular shows.

Day 3: Exploring Oakville’s Natural Beauty and Local Flavors

Morning: Royal Botanical Gardens

Start your final day with a visit to the nearby Royal Botanical Gardens. Although technically located in Burlington, it’s just a short drive from Oakville and well worth the trip. The gardens cover over 1,100 hectares and feature a stunning array of plants and flowers. There are several trails to explore, as well as indoor and outdoor exhibits.

Highlights: Don’t miss the Rock Garden and the Mediterranean Garden.

Tip: Wear comfortable shoes as there’s a lot to see and do here.

Late Morning: Visit a Local Farmers' Market

On your way back to Oakville, stop by one of the local farmers' markets (if visiting on a Saturday). The Oakville Farmers' Market is a great place to sample fresh produce, baked goods, and artisanal products. It’s also an opportunity to chat with local vendors and learn more about the community.

Location: Downtown Oakville, typically at Towne Square.

Seasonal: The market is usually open from late spring to early fall.

Lunch: Brunch at Kerr Street Café

Head back to town for brunch at Kerr Street Café. This popular spot is known for its delicious brunch menu and laid-back vibe. Whether you’re in the mood for a classic eggs benedict or something more adventurous like their avocado smash, you won’t be disappointed.

Recommendation: Their buttermilk pancakes and matcha lattes are crowd favorites.

Afternoon: Art and Culture at Joshua Creek Heritage Art Centre

Spend your afternoon exploring Oakville’s art scene at the Joshua Creek Heritage Art Centre. This unique venue is located on a picturesque 12-acre property and showcases a variety of art exhibits, workshops, and cultural events. The peaceful setting and inspiring artwork make it a great place to unwind and reflect on your weekend.

Activities: Walk through the gallery, explore the outdoor sculpture garden, or join a drop-in art class.

Evening: Farewell Dinner at Cucci Ristorante

Wrap up your perfect weekend in Oakville with a farewell dinner at Cucci Ristorante in Bronte Village. This upscale Italian restaurant offers an intimate dining experience with a menu that includes classic dishes like homemade pasta, fresh seafood, and decadent desserts.

Highlight: Their tiramisu and selection of Italian wines are the perfect way to end your meal.

Atmosphere: The warm, elegant decor and live piano music create a romantic and sophisticated ambiance.

Nightcap: The King's Arms

If you’re not ready for the night to end, stop by The King's Arms for a nightcap. This traditional British pub has a cozy atmosphere, a great selection of beers and whiskies, and live music on the weekends.

Tip: Enjoy the outdoor patio if the weather is pleasant.

Final Thoughts

Oakville’s blend of natural beauty, cultural attractions, and culinary delights make it an ideal destination for a weekend getaway. Whether you’re exploring the historic downtown, enjoying the waterfront, or indulging in the local food scene, there’s something for everyone in this charming town. This itinerary offers a balance of relaxation, adventure, and culture, ensuring that you experience the best that Oakville has to offer. So pack your bags, bring your sense of adventure, and get ready to discover the perfect weekend in Oakville.