What To Do This Weekend in Durham Region (Sept-18-20, 2026)

Looking for things to do this weekend in Durham Region? The third weekend of September is one of the best of the fall season, and this year it is headlined by the Winding Roads Festival and Concert Series in Port Perry on Saturday. Add the 171st Beaverton Fall Fair in Brock Township from Friday to Saturday, Whitby's free Brooklin Harvest Festival on Saturday afternoon, and the free Convergence Music + Art Festival in downtown Oshawa all weekend, and you have a packed third weekend of September. Here is your weekend guide for Friday, the 18th, through Sunday, the 20th.

Friday, Sept-18

Kick off the weekend with opening day at the Beaverton Fall Fair, then a glowing dragon boat paddle and street music in Port Perry.

Beaverton Fall Fair, Opening Day

The 171st Beaverton Fall Fair opens Friday at the Beaverton Fairgrounds (176 Main Street) in the village of Beaverton, in the Brock community. This year's theme is Stitch and Grow, Put on a Show. Expect a full midway with carnival rides, agricultural displays and competitions, livestock and homecraft exhibits, food vendors and family entertainment. Tickets are $15 for adults, $5 for kids 4 to 14 after 6 PM (free before), with advance weekend passes around $25 and free parking. Check the official fair website for the schedule.

Port Perry Glow Paddle

Friday evening, the Scugog Dragon Boat Club hosts the 5th Annual Port Perry Glow Paddle, a night paddle of LED-lit dragon boats on Lake Scugog. Rowers gather at the waterfront in the evening for a spectacular glowing procession across the lake. Details and timing are on the event listing. It is a memorable way to see Port Perry from the water, and the town's Port Perry community is at its liveliest on these late-summer evenings.

If you are staying closer to shore, the Songs of Summer free street music series runs weekends through September in downtown Port Perry, with local musicians performing along Queen Street. It is a relaxed way to ease into the weekend with a lakeside stroll.

Saturday, Sept-19

Saturday is the biggest day of the weekend, headlined by the Winding Roads Festival in Port Perry. Add the fair's full slate, a free harvest festival in Whitby, the start of Convergence in Oshawa, and the Port Perry farmers market all on the go.

Winding Roads Festival and Concert Series (Headline)

The biggest event of the weekend is the Winding Roads Festival and Concert Series on Saturday, September 19, in Port Perry. This is the 11th anniversary of the live music fundraiser for Big Brothers Big Sisters of North Durham, and the 2026 festival is headlined by the Steve Waters Band, with Red Cup County among the special guests. Proceeds support Big Brothers Big Sisters mentoring programs across North Durham, so every ticket directly helps local youth. For the lineup, schedule and tickets, visit the Winding Roads page on the Big Brothers Big Sisters site or the dedicated Winding Roads website.

Beaverton Fall Fair, Parade and Derby Day

Saturday is the fair's biggest day in Beaverton. The day features the fair parade, a car show, a demolition derby, the baby show and a full slate of agricultural competitions, along with the midway and family entertainment. See the Beaverton Fall Fair site for the day-by-day schedule, since many events run only once.

Brooklin Harvest Festival in Whitby

The Brooklin Harvest Festival celebrates the fall season Saturday from 10 AM to 4 PM at Grass Park (41 Baldwin Street) and along downtown Brooklin in Whitby. This free event brings local vendors, family activities, seasonal food, live music and a warm small-town atmosphere. It is a lovely reason to explore the village of Brooklin, which is part of the Whitby community. Details are listed on the fall harvest festivals roundup.

Convergence Music + Art Festival in Oshawa

Downtown Oshawa comes alive Saturday and Sunday for the Convergence Music + Art Festival along King Street. This free festival showcases local and national musicians, live art, installations and creative programming for all ages, a celebration of the Oshawa community's arts scene. See the Convergence Oshawa website for the full lineup and stage locations.

Port Perry Lakefront Farmers' Market

The Port Perry Lakefront Farmers' Market runs from 8 AM to 3 PM at the foot of Queen Street on Lake Scugog. It is one of the largest markets in Durham Region, with farm-fresh produce, meats, artisan baking, crafts, honey and maple syrup, plus live entertainment. Pick up early-fall apples and squash, then stroll the historic Queen Street shops in the Port Perry community or walk the waterfront nearby. See the market's website for vendor news.

Scugog Arena 50th Anniversary

In Port Perry, the Scugog Arena marks 50 years with a Community Open House and a 50th Anniversary Dance at the Scugog Community Recreation Centre (1655 Reach Street). It is a family-friendly way to celebrate a beloved local landmark. Details are on the Township of Scugog events page.

Pawsitive Fair in Whitby

Animal lovers can head to the Pawsitive Fair 2026 in Whitby on Saturday starting at 11 AM at the Ontario SPCA Durham Region Animal Centre (1505 Wentworth Street). This pet-friendly gathering brings local vendors, a bake sale, raffles and adoptable animals, a cheerful addition to a busy Saturday.

Sunday, Sept-20

Close out the weekend with a second day of music in Oshawa, a live show in Port Perry and the Uxbridge farmers market.

Convergence Music + Art Festival, Day Two

The Convergence Music + Art Festival wraps up its run Sunday in downtown Oshawa along King Street. With free performances and art programming all day, it is a relaxed way to spend a late-summer afternoon in the Oshawa community. Confirm stage times on the Convergence website.

Eternal Embrace LIVE in Port Perry

Music fans in Port Perry can catch Eternal Embrace LIVE on Sunday at Prince Albert Hall, a cherished heritage venue on Queen Street in the Port Perry community. It is a lovely chance to enjoy live performance in one of the region's most historic rooms.

Uxbridge Farmers' Market

The Uxbridge Farmers' Market runs Sunday from 9 AM to 2 PM at 14 Victoria Street, beside The Second Wedge Brewing Co. Expect local produce, artisan baking, crafts and live music from the market's vendors. Its 2026 season runs through late October, so there is plenty of time to enjoy it in the Uxbridge community. See the market's website for the vendor lineup.

Plan Your Weekend

Whether you are singing along at the Winding Roads Festival in Port Perry, riding the midway at the Beaverton Fall Fair, browsing the Brooklin Harvest Festival, catching live music in downtown Oshawa, or stocking up at the Port Perry farmers market, there is plenty to do across Durham Region this weekend. New to the area? Our Port Perry community guide and Brock community guide are great introductions to the towns hosting the biggest events, and our Weekend Guide archive has every edition we have published so far.

If a slower weekend sounds better, the Port Perry waterfront and Lake Scugog trails are always open, and the honest guide to country living in Durham Region explains what day-to-day life looks like near these communities. Wherever your weekend takes you, we hope you have a safe and happy one in our beautiful Durham Region.