Ya Can't Miss This

The Main Tract at Dufferin County Forest hosts a run of permitted events through to the middle of October. They’re worth entering — and worth knowing about if you’d rather have the trails to yourself.

Dates	Event
July 8–13	OTRA Horseback Riding
July 17–20	OCTRA Horseback Riding
August 4–10	OTRA Horseback Riding
August 29–30	Substance Projects Bike Race
September 4–7	OTRA Horseback Riding
September 18–21	Chesley Saddle Club
October 2–5	OCTRA Horseback Riding
October 16–19	Chesley Saddle Club

The forest stays open year-round outside these events — 1,066 hectares across 14 tracts for hiking, mountain biking, cross-country skiing and horseback riding, free to enter. If you only have an hour, the Mono Tract is much closer to town than the Main Tract.

Full guide to Dufferin County Forest →

Trail maps and permit enquiries: dufferincounty.ca/forest · forest@dufferincounty.ca · 519-941-1114 ext. 4011

Mono Tennis Club’s junior programs run Tuesdays for seven weeks, starting July 28, on the courts at Mono Centre Park. Rather than one mixed session, there’s a separate stream for each age and stage:

• Orange Ball — ages 5 to 8, 4:00–5:00pm. Built for beginners: games, activities, hand–eye coordination, and lower-compression orange balls on smaller courts so rallies actually happen.
• Green Ball — ages 9 to 12, 5:00–6:00pm. Technique, consistency, court movement, match play and sportsmanship, played with green balls on full-size courts.
• Teen Tennis — ages 13 and up, 6:00–7:00pm. Advanced technique and tactics, drills and match play, fitness and agility — aimed at school, club and tournament play.

$197.75 per player. Registration is through the club’s online form, and the first session is this Tuesday, so spots won’t last.

Register for a junior program · Mono Tennis Club website

The club’s season runs May through October, and family memberships are available if your kids catch the bug.

The Big Dufferin Play Day runs at the Alder Recreation Centre on Sunday, August 9, noon to 5:00 p.m. — five hours of outdoor family fun, and the kind of afternoon where the kids run themselves flat out and sleep well that night.

What’s on

• Bouncy castles
• A petting zoo
• Princess meet-and-greets
• Face painting
• Live entertainment
• Food vendors
• A local marketplace and kids’ market

Ticketed, and for a cause

This one is ticketed, and the organisers say tickets are moving — worth sorting before the day rather than turning up and hoping.

It runs in support of Dufferin Child & Family Services, who work with children, youth and families right across the county. So it is a fundraiser as much as a day out.

Questions go to bigdufferinplayday@gmail.com.

Shelburne’s Fiddle Park Concert Series runs Sunday evenings at 6:00 p.m., and every night of it is free.

What’s still to come in 2026

Date	Who’s playing
Sunday, August 9	Matlockes & Amy Winehouse
Sunday, August 16	Almost Hip
Sunday, August 23	Tyler Reed & Aubry FillHarmonics
Sunday, September 13	Whiskey Rocks

The series opened on July 12 with a ribbon cutting, Bhangra dancers, and the Campfire Poets with fiddler Aaron Solomon, followed on July 19 by Exodus — a Bob Marley tribute featuring Lazo.

Plan your visit

• Fiddle Park, 105 County Road 11, Shelburne
• Free admission, and family-friendly
• Bring your own blankets — or a lawn chair
• It’s outdoors, so dress for the weather

Why this park, this year

Fiddle Park has just been redeveloped under the Town’s Parks and Recreation Master Plan, and the concert series is the first real test of it as a gathering place. These are the same grounds that host Pickin’ in the Park and that gave Shelburne the Fiddleville name — so a summer of free live music there is the town leaning into what it has always been known for.

The Town describes the series as an annual initiative meant to grow year over year, with a deliberately wide range of genres rather than one style. The Town’s own page answers the practical questions — dogs, lawn chairs, alcohol, picnics, washrooms, parking, and what happens if it rains.

A separate Fiddle Park Movie Night follows on Friday, August 29 at 8:30 p.m.

Local performers: the Town wants to hear from you

Shelburne is building a roster of artists for the 2027 series and other community events, and it’s open to performers of all genres and styles.

Email jhanzel@shelburne.ca with your name or group name, the type of performance, and links, samples or demos of your work.

If you know someone locally who should be on that stage, pass it along — this is the kind of thing that gets filled by whoever hears about it.

Great Canadian Wrestling runs two separate cards at the Orangeville Curling Club on Sunday, August 9, and Battleground is the evening one — 5:00 to 7:00 p.m., built around two rings and a steel cage.

This is the one to bring the kids to

The two shows that day are aimed at completely different audiences, and it is worth getting right:

	Battleground — 5 p.m.	GCW Extreme — 1 p.m.
Audience	”Bring your friends. Bring your family.”	16+ advised, rated “B for Blood”
Kids’ tickets	$25, 12 and under	Not a kids’ show

Same venue, same afternoon, opposite ends of the spectrum. If you turn up expecting a family outing, you want the 5 o’clock.

Tickets

• $25 — general admission, kids 12 and under
• $30 — general admission, adult
• $40 — front row reserved (online only)
• +$25 — VIP add-on, on either ticket: GCW gift bag, pins and a programme

It is also a charity event, with GCW supporting local causes.

Great Canadian Wrestling brings GCW Extreme to the Orangeville Curling Club on Sunday, August 9, 1:00 to 3:00 p.m.

This is not a family show. GCW bills it as a hardcore card, rates it “B for Blood”, and advises against bringing anyone under 16.

If you were planning to bring kids, you want the other one. GCW runs a second, separate card at the same venue that evening — Battleground at 5:00 p.m. — which is the family show, with tickets priced for 12-and-under. Two shows, one afternoon, opposite ends of the spectrum.

Tickets are $25 general admission, $40 for front-row reserved (online only), with a VIP add-on at $25 more that includes a gift bag, two GCW pins and a programme.

It doubles as a food drive. Bring non-perishable items and you get raffle entries — up to ten per person. The organisers have asked specifically for school snacks, juice, canned goods, cereal, toiletries, pet food and baby supplies.

The Shelburne Muskies are holding five tryout skates through August and September as they build their roster for the coming OEHL season.

They are recruiting elite, pro, CHL, NCAA and Jr A, B and C talent — so this is a serious look, not a rec-league sign-up.

The schedule

Date	Time	Rink
Mon 10 August	9:00–10:30 p.m.	Alliston NTRC
Mon 17 August	9:00–10:30 p.m.	Alliston NTRC
Mon 24 August	9:00–10:30 p.m.	Alliston NTRC
Wed 2 September	8:30–10:00 p.m.	Nottawasaga Centre Ice Sportplex
Wed 9 September	8:00–9:30 p.m.	Nottawasaga Centre Ice Sportplex

$25 per skate. Register at shelburnemuskies.ca, or email ShelburneMuskiesOEHL@gmail.com.

One thing worth knowing before you go

The tryout ice is not in Shelburne. Both rinks are over in Simcoe County — the NTRC in Alliston and the Nottawasaga Centre Ice Sportplex — so budget roughly forty minutes each way from town. The team is Shelburne’s; the ice they could book for late-evening skates in August is not.

Who the Muskies are

Shelburne’s senior club plays in the Ontario Elite Hockey League, a 19-team OHA-affiliated circuit billed as the largest senior league in the province. They joined for the 2025–26 season and play in the North Division.

If you would rather watch than skate, their golf tournament is on 27 September, and the season follows.

Grandparents get in free at the Museum of Dufferin from Tuesday, August 11 through Saturday, August 15, when accompanied by someone under 18. Open 10:00 a.m. to 4:00 p.m. daily.

Five days to walk the Home & Heritage photography exhibition together before it closes in September — and a good excuse for the drive up Airport Road.

Amaranth puts its whole year into one Wednesday evening this month, and it is worth the drive out.

The 172nd Anniversary Community BBQ runs 5:00 to 8:00 p.m. at the Municipal Park, and everything at it is free: a bouncy castle, soccer darts, a photo booth, a vendor market, and a Bike Roadeo — a skills-and-safety course for kids on their own bikes. The Roadeo is the one part that wants registering for in advance.

The Amaranth Community Market runs 6:00 to 8:00 p.m. the same evening, in the same park. It is the last of three this summer, after June 10 and July 8.

Amaranth is one of the quieter corners of the county and it does not get a lot of listings. This is the night it puts everything on.

The 3rd Annual Dufferin Film Festival runs August 14–16, 2026 at the historic Orangeville Opera House. Celebrating Canadian independent cinema with short film screenings in all genres. The 2025 festival sold out — early tickets strongly recommended. Weekend includes Opening Night red carpet screening (Friday), VIP Social at Revival 1863, Saturday morning industry Speaker Series, and VIP Awards Night on Sunday. Tickets and full schedule at dufferinfilmfest.com.

The fourth annual Lynda Hollran-Thompson Memorial Concert takes place Saturday, August 22 from 5:00 p.m. on Hockley Road in Mono — an evening of live music held in Lynda’s memory, in about as good a rural setting as the county offers.

This is a community-run evening rather than a festival, and it is exactly the sort of thing that never makes the tourism calendars. Tickets and details through Eventbrite.

The final Fridays in the Park of 2026 lands on Friday, August 28, from 6:00 to 9:00 p.m. at Jack Downing Park in downtown Shelburne.

Live music, entertainment for the kids, and the sort of evening where the whole downtown feels busy. Free to attend, no tickets, just turn up.

Three earlier dates — June 12, June 13 and July 10 — have already passed, so this is the last one until next summer.

Full guide to the series, including what it’s actually worth to Shelburne →

The 21st annual Jim Cuddy Jamboree comes to Lyric Pond in Mulmur on Thursday, September 3 at 6:00 p.m.

A Blue Rodeo frontman playing a fundraiser in a Mulmur field is not a normal September Thursday around here, and this one has been running for two decades. Music and food, outdoors.

This year’s proceeds go to the Honeywood Arena renovation — the same project behind the Fore Honeywood Golf Classic later in the month. The North Dufferin Community Centre at Honeywood is Mulmur’s only indoor recreation complex, so the arena work matters more locally than a single building usually would.

Ticketed. Check ahead for availability — a 21-year-old event with a name like that on the bill does not always have tickets at the gate.

Country fair and fun for everyone, over three days at the OAS Event Centre.

Day	Hours
Friday 4 September	4:00 p.m. – 11:00 p.m.
Saturday 5 September	9:00 a.m. – 11:00 p.m.
Sunday 6 September	9:00 a.m. – 10:00 p.m.

Demolition derby, beer tent, live entertainment, midway rides, Kids Zone, food vendors, wagon rides, free face painting for children, home craft displays and plenty more.

Where it actually is: despite the name, the fair runs at the OAS Event Centre on 5 Sideroad in Mono, not in downtown Orangeville. Set your GPS to 247090 5 Sideroad, L9W 6K5 — about ten minutes north of Broadway.

Paid admission. Tickets and the full schedule at oaseventcentre.ca, or call 519-942-9597.

A one-hour guided walk through the Museum of Dufferin’s summer gardens with museum staff, Saturday, September 5 from 2:30 to 3:30 p.m.

Small, seasonal, and included with admission. Details at dufferinmuseum.com.

Saturday, September 12 at the Caledon East Community Complex — billed as Caledon’s largest sporting event, and open to anyone who wants to sign up.

The Marathon of Sport is a full day of inclusive sport, where participants of all abilities compete on the same field, in support of the Special Olympics Canada Foundation.

It is over the county line, about half an hour from Orangeville. Worth knowing about anyway: there is nothing of its kind inside Dufferin, and it is the sort of day that takes a team rather than a spectator.

The second annual FORE Honeywood golf classic runs Thursday, September 17 at the Shelburne Golf & Country Club, in support of the Honeywood Arena Renovation Fund.

What’s included

• Shotgun start, scramble format
• Lunch provided on the turn
• Golf carts included
• Swag bags and on-course contests
• Raffle and prizes

Rain or shine.

Why the arena matters

The money goes to essential upgrades at Honeywood Arena — repairs and new dressing rooms, to keep it safe and accessible. The North Dufferin Community Centre at Honeywood is Mulmur’s only indoor recreation complex, which is why a rural arena renovation draws two separate fundraisers in the same month.

The other is the Jim Cuddy Jamboree on September 3, for the same fund.

Registering

Registration is through the Township of Mulmur’s online store. Sponsorship opportunities are available if you would rather back it than play it.

The Shelburne District Fall Fair returns September 18–20, 2026, with this year’s theme: Harvest, Honey, & Home.

Three days of the things that have anchored this fair for generations — the Dairy, Beef Cattle, Sheep, Calf Club and 4-H Sheep shows, the Kid Zone, the Baby Show, the midway, and the agricultural exhibits that quietly showcase how much of Dufferin’s economy still comes out of the ground.

Held on the second weekend after Labour Day, as always. General parking is at the Centre Dufferin Recreation Complex and Glenbrook Elementary School. Full schedule and fair book at shelburnefair.weebly.com, or call Sue Peterson at 519-217-5606.

Saturday, September 19 at the Museum of Dufferin, and admission is by donation — which makes it one of the better value days out this autumn.

Earth & Fire puts clay and glass side by side: sculpted pottery and blown glass, as art and as things you can actually use.

What’s on

• Clay and glass vendors, with work for sale
• Drop-in crafts for kids — no booking
• Pre-registered adult workshops — ticketed separately
• Silent auction art fundraiser
• Access to all the Museum’s galleries and exhibitions, including the W. J. Hughes Corn Flower Glass Exhibition

That last one is worth the trip on its own. The Corn Flower collection is a genuinely significant piece of Canadian glass history and it lives here, in Mulmur.

Applying as a vendor

The Museum runs an open call at dufferinmuseum.com/earthandfirecall.

The MoD is at 936029 Airport Road. Its own site is difficult to read for event detail, so if you want to confirm workshop tickets, phone 519-941-1114.

Mill Street shuts down on Saturday, September 19 for Oktoberfest in Downtown Orangeville — noon until 11:00 p.m., steins, live music, food, and the downtown core about as busy as it gets all year.

Run by the Downtown Orangeville BIA. Details at downtownorangeville.ca.

The 154th Grand Valley Fall Fair runs September 25 to 27 at the fairgrounds on Main Street North.

A hundred and fifty-four years is not a number many events in this county can put next to their name. It is a working agricultural fair rather than a midway with a farm theme — livestock, homecraft and community classes, in a village that still farms.

It is also the last of the county’s three fall fairs, after Orangeville on the Labour Day weekend and Shelburne the week before. If you are going to make a season of them, this is the closer.

Fair contact: 226-979-3724.

Great Canadian Wrestling returns to Dufferin in the autumn, this time in Shelburne — the Centre Dufferin Recreation Complex on Sunday, September 27, from 6:00 p.m.

GCW runs a circuit of these across Ontario and lands in the county more than once a year; this is the Shelburne stop, following their August double-header in Orangeville. Tickets are through Eventbrite.

It shares the day with the Shelburne Muskies Golf Tournament, which tees off in the morning — so if you are the sort of person who would happily do both, September 27 is your day in Shelburne.

Not yet published: ticket prices, the card, and whether this one is family-friendly or a hardcore show. GCW’s Orangeville dates run both kinds, so it is worth checking the Eventbrite listing before bringing children.

A day on the links in support of senior hockey. The Shelburne Muskies’ second annual tournament was rescheduled from July 18 because of the forecast, and registration has reopened for the new date — Sunday, 27 September 2026.

Start	8:30 a.m. shotgun
Format	Best ball, 18 holes
Included	Cart, plus lunch at the turn
Non-member	$150 per golfer
Member	$93 per golfer

Sponsorship packages run from $250 to $5,000 and are still available — worth a look if you’re a local business wanting to put your name in front of a few hundred people who follow the team.

All proceeds support the 2026-27 Muskies season — the Shelburne Muskies are a Senior AA club at the Centre Dufferin Recreation Complex, and one of the town’s oldest sports organisations at close to ninety years old.

Register or sponsor → · shelburnemuskies.ca · Meet the team →

The course is just outside town in Melancthon, so set your GPS to the club rather than to Shelburne itself.

Downtown Orangeville’s family Halloween morning returns Saturday, October 17, from 9:00 a.m. to 1:00 p.m. Costumes on, trick-or-treating at participating Broadway businesses, and activities up and down the street.

Free to attend, run by the Downtown Orangeville BIA, and reliably one of the best-attended mornings of the fall.

Mono’s 3R Christmas Bazaar takes over the Monora Park Pavilion on Saturday, November 14, 10:00 a.m. to 4:00 p.m.

An indoor maker and community market at the point in the year when the outdoor ones have finished — which is most of what recommends it. The Grand Valley Makers Market wraps up in August and the farmers’ market closes in October, so November onward is thin for this kind of thing.

The pavilion sits in Monora Park, so there are eighteen kilometres of trails outside if you want to walk off the shopping.