As Ontario road trip experts, we’ve spent countless hours researching, scouting, and personally experiencing destinations across the province -- and Collingwood continues to stand out as a favourite.
That’s exactly why we’re here to share our top picks for the best things to do in Collingwood, based on real road trips, not just a quick Google search.
Many of these stops are ones we feature in our Markets to Mountains road trip a one day surprise road trip that can depart from Toronto, Kitchener-Waterloo, London, or Sarnia and winds through charming small towns and hidden gems before ending in Collingwood. It’s designed for travellers who want to explore beyond the obvious tourist destinations and experience these areas like a local.
What is a one day surprise road trip?
At Guess Where Trips, we plan one day surprise road trips that get you out of the house and exploring new things! This small town is just one of many that we recommend on our trips.
The map below marks each stop we recommend during your visit to one of Ontario's most charming small towns.
Table of Contents
1. Head to our favourite brewery: Side Launch Brewing Company
Address: 200 Mountain Rd Unit 1, Collingwood, ON L9Y 4V5
Hours:
Sundays, Tuesdays, & Wednesdays: 12PM-6PM
Thursday-Saturday: 11AM-7PM
Located in the industrial area of Collingwood, you'll love this brewery that invites you to relax, socialize, and of course, try amazing brews. Side Launch Brewing is well known for having a wide variety of beers on tap, including core favourites alongside small-batch brewery-exclusive releases you can only try on site, so there’s always something new to discover!
Along with delicious brews, Side Launch also offers an extensive board game library and shuffleboard, live music every Friday-Sunday, fire pit and pop ups from November-March, and a delicious taco food truck called Mamacita Tacoria that's open from May-September.
Side Launch is just one of many breweries we include in our Markets to Mountains surprise road trip.
💡 Travel Tip 💡
Want to try more craft beer from the area? Side Launch Brewing, along with six other award-winning craft beverage producers, have put together a self-guided tasting tour. Whether you explore on foot, by bike, or by car, it’s a fun way to sip your way through the Collingwood and discover a range of expertly crafted bears, ciders, and spirits along the way.
2. Snap Insta-worthy photos at Sunset Point Beach
Address: 79 St Lawrence St, Collingwood, ON
This iconic location on Nottawasaga Bay is the most beautiful spot to take lots of photos and marvel at the view of the Blue Mountains in Collingwood. During the warmer months, Sunset Point Beach has picturesque trails along the water, green space, and volleyball courts. In the winter, the shores are blanketed with snow surrounding a giant stone Inukshuk, where you can see the Niagara Escarpment behind the historic Collingwood Grain Terminals.
💡 Travel Tip 💡
Travelling with kids? If you walk across the street and head eastward you'll find Sunset Point Park (formerly known as Enviro Park) which has a fun and colourful playground with structures centred around Collingwood's features such as a lighthouse, wetland, town hall and village, forest, amphitheatre and beach!
3. Shop at our favourite boutiques in Downtown Collingwood
With over 60 boutique shops in downtown Collingwood, shopping is an attraction all on its own. Here are a few boutiques you won’t want to miss:
Offers a wide selection of locally-crafted, soy-based candles.
Address: 27 Hurontario Street, Collingwood, ON
Hours: Monday-Saturday from 10AM-5PM and Sundays from 10AM-4PM
Men's & women's fashion and accessories.
Address: 69 Hurontario St, Collingwood, ON
Hours: Monday-Saturday 11AM-6PM; Sunday 11AM-4PM
Offers stylish, eco-friendly and Canadian-made women’s clothing.
Address: 126 Hurontario St unit B, Collingwood, ON
Hours: Monday-Thursday from 10AM-5:30PM; Friday-Saturday 10AM-6PM; Sunday 11AM-5PM
Women’s and children’s clothing, accessories, and home decor items in muted/neutral tones.
Address: 115 Hurontario St, Collingwood, ON
Hours: Monday-Friday 10AM-6PM; Saturday 10AM-5PM; Sunday 11AM-4PM
Custom designed decor, apparel, and gifts based on the cottage lifestyle.
Address: 151 Hurontario St, Collingwood, ON
Hours: Monday-Saturday 10:30AM-4:30PM; Sunday 11AM-4PM
4. Learn Collingwood's history at a train station from 1873
Address: 45 St. Paul St., Collingwood, ON
Hours: Tuesday-Saturday, 10AM-4PM
The Collingwood Museum, originally a train station in 1873, is a great spot to take in the town’s history, with exhibits that highlight its shipbuilding roots, Indigenous history, and the people who helped shape the area. It’s an easy stop to pair with a walk along the harbour and a great way to add a bit of local context to your visit. Don’t forget to stop by the gift shop on the way out to see its selection of small gifts, prints, post cards, books, games, and more.
5. Have a picnic at The Collingwood Arboretum
Address: 6 Hickory Street #3E5 off, First St, Collingwood, ON
Tucked just outside of the downtown core, The Collingwood Arboretum is a peaceful park that offers paved and natural trails for hiking, biking, or a leisurely stroll. Its diverse collection of trees, flowers, and plants make it a great spot for a picnic in the warmer months.
💡 Travel Tip 💡
If you head north from the Arboretum parking area and follow the path toward Harbourview Park, you’ll find The Collingwood Labyrinth - a community-funded installation made of carefully placed stones forming a walking path designed for reflection and mindfulness. There's also a plaque nearby that explains the symbolism behind the labyrinth and how to walk it!
Markets to Mountains
Explore Collingwood and more on this mystery road trip that can be taken from Sarnia, London, Toronto, and Kitchener-Waterloo.
6. Taste our favourite restaurants and bars
Collingwood is home to a strong mix of independent restaurants and bars that highlight fresh ingredients and creative menus. If you’re able to stay for dinner, we recommend:
A Mediterranean inspired restaurant
Address: 172 Hurontario St, Collingwood, ON
Hours: Monday, Wednesday, Thursday 5:30PM-8:45PM; Friday-Saturday 5PM-9:45PM; Sunday 5PM-8:45PM *Reservations required
Cozy & intimate Italian restaurant
Address: 27 Fourth St E, Collingwood, ON
Hours: Tuesday-Saturday 5PM-10PM
Mexican restaurant serving tacos, burritos & cocktails
Address: 48 Pine St, Collingwood, ON
Hours: Monday-Tuesday 5PM-9PM; Wednesday-Saturday 12PM-9PM; Sunday 12PM-8PM
Cafe & Bottleshop offering wine, beer, cider, and mead.
Address: 93 Hurontario St Unit 3, Collingwood, ON L9Y 2L9
Hours: Monday-Thursday, Sunday 8AM-4PM; Friday-Saturday 8AM-12AM
Bar offering a mix of Asian-inspired snacks and cocktails
Address: 65 Simcoe Street, Unit 5, Collingwood ON
Hours: Monday-Saturday 4PM-9:30PM
Take-out gourmet burgers
Address: 316 Hume St, Collingwood, ON
Hours: Monday-Sunday 11AM-8PM
💡 Travel Tip 💡
As Collingwood is a popular destination, we highly recommend booking dinner reservations ahead of time to ensure you get a table!
7. Snap a picture in front of the CWOOD sign
Address: 97 Hurontario St, Collingwood, ON L9Y 2L6
Standing in front of the Town Hall, the iconic CWOOD sign lights up the space and shifts its colours with the seasons. Behind it, the Town Hall building (originally a market and opera hall) features Romanesque Revival architecture and rises three storeys tall, topped by a clock tower added in the 1890s that can be spotted from all around town.
8. Visit the Royal Canadian Legion Branch 63
Address: 490 Ontario St, Collingwood, ON L9Y 1N6
The Royal Canadian Legion Branch 63 is a community hub dedicated to honouring Canada’s veterans while bringing locals together through events, programs, and shared traditions.
In the parking lot, you’ll find an F-96 Starfire aircraft and a Sherman tank that you can walk right up to.
Our Markets to Mountains road trip provides lots of background information on historic stops like these!
9. Take a detour to Blue Mountain Village
Address: 156 Jozo Weider Blvd, The Blue Mountains, ON
Of course, no visit to Collingwood would be complete without stopping by its most popular nearby attraction: Blue Mountain Village. This vibrant, pedestrian-friendly destination is just minutes from downtown Collingwood, and offers something for everyone -- in every season. In the winter months, visitors can enjoy skiing and snowboarding, scenic gondola rides, and cozy apres-ski dining throughout the village. In the warmer months, the area offers great hiking and biking trails, mountain coasters, outdoor patios, and more.
Our Markets to Mountains road trip has lots of "want to keep going" suggestions for those who want to spend more time in Blue Mountain!
Staying Overnight in Collingwood?
Doing Markets to Mountains and want to stay overnight in Collingwood? Every Guess Where Trip includes several recommendations for places to stay in the area of your fourth stop!
