Oakville

Day Trips

Make the most of your day with our curated plans, packed with Oakville's hidden gems and unique experiences!

day 1
Exploring Historic Center
morning
:

Start your day with a leisurely breakfast at a charming café in the heart of Oakville, where you can enjoy fresh pastries and locally roasted coffee. After breakfast, take a stroll through the historic district, admiring the beautiful architecture and quaint shops that line the streets. Don’t forget to visit the local museum to learn about the rich history of Oakville and its significance in the region.

afternoon
:

After lunch at a farm-to-table restaurant, continue your exploration by visiting the Oakville Arts Center, where you can view contemporary art exhibits and perhaps catch a live performance. Spend some time wandering through the local artisan market, where you can find handmade crafts, jewelry, and delicious local produce. As the afternoon winds down, relax in one of Oakville's picturesque parks, soaking in the natural beauty and tranquility.

evening
:

As the sun sets, dine at a cozy bistro known for its seasonal dishes and local wines. Post-dinner, take a leisurely walk along the waterfront, enjoying the beautiful views of the lake and the starry sky. End your evening with a stop at a local ice cream shop, indulging in a sweet treat to cap off a wonderful day.

day 2
Beach and Water Sports
morning
:

Head to Oakville's nearby beach for a refreshing morning swim in the lake, surrounded by soft sand and the sounds of nature. After swimming, enjoy a beachside brunch with fresh fruit, smoothies, and light bites at a local beachfront café. Take some time to relax on a towel, soaking up the sun and enjoying the vibrant atmosphere.

afternoon
:

Rent a kayak or paddleboard for an exciting afternoon on the water, exploring the beautiful shoreline and possibly spotting some local wildlife. Join a guided water sports lesson if you're feeling adventurous, learning new skills while having fun. Afterward, unwind with a picnic lunch on the beach, savoring the flavors of Oakville's local delicacies.

evening
:

As evening approaches, enjoy a beachfront barbecue where you can grill your own meal while enjoying the stunning sunset over the lake. Gather around a bonfire with friends or family, sharing stories and making s'mores under the stars. Conclude your day with a relaxing stroll along the beach, taking in the calm waves and the gentle night breeze.

day 3
Wine Tasting and Vineyard Tour
morning
:

Start your day with a scenic drive to one of Oakville's renowned vineyards, breathing in the fresh countryside air. Upon arrival, enjoy a guided tour of the vineyard, learning about the winemaking process and the unique characteristics of the local grapes. Sample a selection of breakfast wines paired with artisanal cheeses for a unique culinary experience.

afternoon
:

Continue your vineyard adventure with a delightful wine tasting session, where you can savor a variety of local wines while enjoying beautiful views of the vineyard. Participate in a food and wine pairing workshop, learning how to match flavors to enhance your dining experiences. Afterward, enjoy a leisurely lunch at the vineyard's restaurant, featuring seasonal dishes made with local ingredients.

evening
:

As the sun sets, enjoy a romantic dinner at the vineyard's fine dining restaurant, complete with a carefully curated wine list. Take a moment to stroll through the vineyard as the day comes to a close, taking in the tranquil ambiance and stunning views. End your evening with a nightcap back at the tasting room, reminiscing about the day's experiences.

day 4
Nature Hike and Scenic Views
morning
:

Gear up for a morning hike in the Oakville Nature Reserve, where you can immerse yourself in the beauty of the local flora and fauna. Follow well-marked trails that lead you through lush forests and along serene lakes, providing numerous opportunities for wildlife spotting. Bring along a packed breakfast to enjoy at a scenic overlook, taking in the breathtaking views.

afternoon
:

After your hike, take a break for lunch at a nearby café, savoring hearty meals that replenish your energy. Spend the afternoon exploring the nature reserve further, perhaps participating in a guided nature walk to learn more about the local ecosystem. Capture the stunning landscapes with your camera, ensuring you have memories to take home.

evening
:

As evening approaches, head back to Oakville and visit a local brewery for a casual dinner featuring craft beers and delicious pub fare. Enjoy the lively atmosphere while playing board games or chatting with locals about their favorite hiking spots. Conclude your day with a peaceful walk in a nearby park, reflecting on the beauty of nature you experienced throughout the day.

day 5
Cultural Exploration and Local Cuisine
morning
:

Begin your day with a visit to the Oakville Cultural Center, where you can explore local artwork and historical exhibits. Engage with local artists or attend a morning workshop that showcases traditional Oakville crafts and techniques. Afterward, enjoy breakfast at a nearby café, sampling local specialties to fuel your day.

afternoon
:

In the afternoon, participate in a culinary class focused on Oakville's traditional dishes, where you can learn to prepare and cook local favorites. After the class, enjoy the fruits of your labor with a communal lunch, sharing stories and experiences with fellow participants. Finish the afternoon by exploring local shops that specialize in artisanal foods, perfect for gathering souvenirs.

evening
:

For dinner, make a reservation at a local restaurant known for its innovative take on traditional Oakville cuisine, where each dish tells a story. Enjoy a pre-dinner cocktail at the bar, listening to live music that showcases local talent. End your cultural immersion with a visit to a nearby theater for a local performance or movie screening, rounding out a day filled with creativity and flavor.

day 6
Family Fun at the Amusement Park
morning
:

Kick off your day with a visit to the local amusement park, where excitement awaits around every corner. Start with a hearty breakfast at a nearby diner, fueling up for a day filled with rides and games. Once at the park, make a beeline for the roller coasters and attractions that promise thrills for the whole family.

afternoon
:

After a morning of adrenaline-pumping fun, take a break for lunch at one of the park's family-friendly eateries, offering everything from burgers to cotton candy. Spend the afternoon enjoying the various shows and entertainment options, as well as trying your luck at the carnival games. Capture the joy of the day with family photos at designated spots throughout the park.

evening
:

As evening falls, enjoy a final round of rides as the park transforms into a magical space illuminated by colorful lights. Treat the family to an early dinner at a restaurant just outside the park, sharing laughter and stories about the day's adventures. Conclude your day with a leisurely stroll through the nearby town, perhaps stopping for ice cream before heading back to your accommodations.

day 7
Shopping and Spa Day
morning
:

Treat yourself to a relaxing morning at a local spa, where you can enjoy a rejuvenating massage or facial to start your day off right. After your spa treatment, have a light breakfast at a nearby café, savoring fresh smoothies and pastries. Take your time to unwind and enjoy the serene atmosphere before heading out for some retail therapy.

afternoon
:

Spend your afternoon exploring Oakville's charming boutiques and shops, where you can find unique clothing, gifts, and artisanal products. Don't miss out on local fashion designers and craftsmen showcasing their works in the vibrant shopping district. Take a break at a cozy tea shop, enjoying a warm beverage while you plan your next shopping stops.

evening
:

As the day comes to a close, indulge in a gourmet dinner at a high-end restaurant known for its innovative menu and chic ambiance. Treat yourself to a cocktail or glass of wine, toasting to a day well spent. Conclude your evening with a stroll through the town, enjoying the twinkling lights and lively atmosphere, perhaps stopping for dessert at a local bakery.

day 8
Exploring Local History and Landmarks
morning
:

Begin your day with a visit to the Oakville Historical Society, where you can delve into the town's rich past through fascinating exhibits and artifacts. Take a guided walking tour to learn about significant landmarks and stories that shaped Oakville's identity. Enjoy a quick breakfast at a local café, energizing yourself for a day of exploration.

afternoon
:

After your morning tour, head to one of Oakville's historic homes that offers guided tours, showcasing the architectural styles and lifestyles of past inhabitants. Enjoy a packed lunch at a nearby park, surrounded by lush greenery and the sounds of nature. Spend the afternoon visiting local galleries and cultural sites, appreciating the art and history of the area.

evening
:

As the day winds down, gather for dinner at a historic restaurant that features recipes passed down through generations. Reflect on the day's discoveries with your companions, sharing your favorite moments. End your evening with a visit to a local ghost tour, uncovering the spookier side of Oakville's history under the moonlight.

day 9
Outdoor Adventure and Sports
morning
:

Kick off your outdoor adventure with a hearty breakfast at a local eatery known for its nourishing dishes, preparing you for an active day ahead. Head to a nearby recreational area for a day filled with sports activities like biking, soccer, or frisbee golf. Join a friendly pickup game to engage with locals and enjoy the community spirit.

afternoon
:

After a busy morning, take a break for lunch at a picnic area, where you can enjoy sandwiches and snacks surrounded by nature. Spend the afternoon trying out more adventurous activities, such as zip-lining or rock climbing at a nearby facility. Capture the excitement of the day with photos and fun moments shared with friends or family.

evening
:

As the sun sets, wind down with a casual dinner at a local grill that offers a relaxed atmosphere and hearty meals. Share stories of your day's activities while enjoying a well-deserved drink. If energy allows, take a sunset walk along a nearby trail, appreciating the beauty of Oakville as the day comes to a close.

Discover Oakville

Read more in our Oakville 2025 Travel Guide.

Oakville Travel Guide