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What’s Happening Around Orangeville: October 15–18, 2026

Looking for something fun to do this weekend? From live music and dancing to Halloween festivities, farmers’ markets and fall farm adventures, there’s plenty happening in Orangeville and surrounding areas!

Events & Fall Activities

Boo! on Broadway & Beyond | Saturday, October 17, 9 a.m.–1 p.m. Downtown Orangeville transforms into a Halloween playground with trick-or-treating, costume activities, entertainment, a DJ dance party, face painting and family fun. Free admission.

Tiny Tots Trick-or-Treat Trail | Saturday, October 17, 10 a.m.–12 p.m. Bring the little ones downtown for a fun Halloween adventure! Visit participating businesses for treats while supplies last.

Orangeville Farmers’ Market | Saturday, October 17, 8 a.m.–1 p.m. It's the final outdoor farmers’ market of the season! Shop local and support your favourite vendors in downtown Orangeville.

Barn Dance & Grand Re-Opening | Saturday, October 17, 7 p.m. Join High Country United Church at 346255 Side Road 15, Mono, for an evening of music featuring Greg Holmes & Friends. Adults $25, children under 12 $10.

Sweet Peas Farm | Fall Farm Fun Enjoy the autumn atmosphere, pumpkins, seasonal flowers and beautiful fall displays. Check with the farm for visiting details.

Downey’s Farm Pumpkinfest | September 19–October 31 Celebrate fall with pumpkin picking, seasonal activities and family fun. Tickets available online only at https://downeysfarm.com.

Maple Syrup Farm Experience & Tasting | Weekend Activity Visit the Maple Syrup Museum of Ontario for a maple-themed farm experience, sweet treats and tastings. Check with the venue for tour availability and admission details.

Live Music & Music Nights

Thursday, October 15

GoodLot: Name That Tune, 7–9 p.m.

The Hatter: Tyler Crockatt, 6:30 p.m.

Broadway Beat: Jam Night, 6:30 p.m.

Tap House: Music Bingo, 7 p.m.

Bar on Broadway: Karaoke with JL.

Lightcaster: The Thursday Social featuring Table for Two, live acoustic music 7–10 p.m.

Friday, October 16

GoodLot: Dead Root Revival, ticketed show.

Tap House: Nick Vescio, 8–11 p.m.

Broadway Beat: New Impossibles, 8 p.m.

Lightcaster: Latin Dance Night with DJ Kush. Dance lessons 7–8 p.m., dancing 8 p.m.–late. $10 entry.

Saturday, October 17

GoodLot: Mark Thackway, 4–7 p.m., plus Dr. Glow Disc Golf Tournament, 6–10 p.m.

Tap House: Under the Covers, 8–11 p.m.

Broadway Beat: Deep Room, 8 p.m.

Lightcaster: Kenny V., 8 p.m.–midnight. No cover.

Sunday, October 18

GoodLot: Ky Anto, 2–5 p.m.

Tap House: Stan Chang, 1–4 p.m.

Broadway Beat: Industry Night Karaoke, 7–11 p.m.

Lightcaster: Sunday Social, Progressive Euchre, 12:30–3:30 p.m.

There's something for everyone this weekend! Get out, explore, support local businesses and enjoy everything our community has to offer.

The Ginny and ‘er’ son Team

Think SOLD – Think Ginny And’er’son

Office: 519-941-5151

Mobile: 519-938-0028

#GinnyAndErSon #SellWithGinny #THINKSOLD #ThinkGinnyAnderson #LocalEvents #OrangevilleEvents #DowntownOrangeville #DufferinCounty #LiveMusic #WeekendEvents #SupportLocal

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I have sold a property at 71 Shirley Street in Orangeville

I have sold a property at 71 Shirley Street in Orangeville on Oct 13, 2026. See details here

Welcome to 71 Shirley Street, a well-appointed detached home in the heart of downtown Orangeville backing onto Myr Morrow Park. Here, everyday convenience meets comfortable family living. Ideally located close to downtown shops, restaurants, parks, schools, trails and local amenities, this 3-bedroom, 3-bathroom home offers a great combination of space and location. The main floor features a large welcoming living room, dining area with French doors walking out to a deck and lovely rear yard, and a functional kitchen! A convenient 2-piece powder room completes the main level. Upstairs, the spacious primary bedroom offers a walk-in closet and updated 3-piece ensuite. The second bedroom features a wall to wall closet, while the third bedroom also enjoys its own walk-in closet. An upgraded 4-piece bathroom serves the additional bedrooms. The finished basement provides a large recreation room with plenty of space for family movie nights, games, a home gym or a comfortable second living area. Step outside to enjoy the backyard, complete with a deck, shed and above-ground pool (seasonal - removed in winter months), offering flexibility for future use of the yard. A great opportunity to enjoy the best of Orangeville living, with the shops, restaurants and amenities of downtown just moments from home. Updates: Shingles 50 yr ('14), Windows in upper floor & living room window (excluding dining and rear door)('16/17'), Main & Upper Laminate Flooring ('21), Furnace, A/C & Heat Pump ('24), Primary Ensuite & Vinyl Flooring ('25), Upper bathroom (except tub/shower)('26), Upper bathroom vinyl plank flooring ('26), Shed ('26).

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WHAT’S HAPPENING AROUND ORANGEVILLE: OCTOBER 8–12, 2026

Looking for something to do this Thanksgiving long weekend? From fall fairs and pumpkin festivals to live music, karaoke, local markets and family-friendly activities, there's plenty happening in and around Orangeville!

EVENTS & THANKSGIVING WEEKEND FUN

Erin Fall Fair | October 9–12 - Celebrate Thanksgiving weekend at the Erin Fall Fair! Enjoy midway rides, agricultural exhibits, farm animals, local vendors and family-friendly entertainment. Visit https://erinfair.com/ for event details and admission information.

Downey's Farm Pumpkinfest | September 19–October 31 - Celebrate fall with Pumpkinfest at Downey's Farm! Enjoy seasonal activities, pumpkins and plenty of family-friendly autumn fun. Tickets are available online only at https://www.downeysfarm.com/

Sweet Peas Farm - Enjoy a fall farm outing with pumpkins, seasonal displays and photo opportunities. A great way to spend time outdoors and enjoy the autumn season!

Orangeville Farmers' Market | Saturday, October 10 - 8 a.m.–1 p.m. | 2nd Street beside Town Hall

Shop fresh local produce, seasonal favourites, baked goods and more while supporting local farmers and vendors.

LIVE MUSIC & ENTERTAINMENT

Thursday, October 8

  • GoodLot: Movie Trivia Night, 7–9 p.m.

  • The Hatter: Ryan Hancock, 6:30 p.m.

  • Broadway Beat: Jam Night, 6:30 p.m. sign-up

  • Tap House: Music Bingo Night, 7–9 p.m.

  • Bar on Broadway: Karaoke, 7 p.m.

  • Lightcaster: Brett Lawler, live acoustic music, 7–10 p.m.

Friday, October 9

  • GoodLot: John Cheesman, 5–7 p.m.

  • Tap House: 1990 A.D., 8–11 p.m.

  • Broadway Beat: Mid-Life Crisis, 8 p.m.

  • Lightcaster: Madchester, 8 p.m.–midnight. No cover!

Saturday, October 10

  • GoodLot: Mark Thackway, 4–7 p.m.

  • Tap House: DJ T1, 9 p.m.–1 a.m.

  • Broadway Beat: Guitars Cadillacs, 8 p.m.

  • Lightcaster: 2000s Throwback Party, 8 p.m.–late.

Sunday, October 11

  • Mono Centre Brewing: Drew Moore, live music, 2–5 p.m.

  • GoodLot: Nick Vescio, 2–5 p.m.

  • Broadway Beat: Industry Night Karaoke, 7–11 p.m.

  • Lightcaster: Open Mic, 4:30–8:30 p.m.

Monday, October 12 – Thanksgiving

Enjoy the holiday with family and friends! The Erin Fall Fair and Downey's Farm Pumpkinfest offer more ways to enjoy the long weekend.

Wishing everyone a wonderful Thanksgiving long weekend!

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Open House. Open House on Sunday, October 4, 2026 12:00PM - 2:00PM

Please visit our Open House at 71 Shirley Street in Orangeville. See details here

Open House on Sunday, October 4, 2026 12:00PM - 2:00PM

Welcome to 71 Shirley Street, a well-appointed detached home in the heart of downtown Orangeville backing onto Myr Morrow Park. Here, everyday convenience meets comfortable family living. Ideally located close to downtown shops, restaurants, parks, schools, trails and local amenities, this 3-bedroom, 3-bathroom home offers a great combination of space and location. The main floor features a large welcoming living room, dining area with French doors walking out to a deck and lovely rear yard, and a functional kitchen! A convenient 2-piece powder room completes the main level. Upstairs, the spacious primary bedroom offers a walk-in closet and updated 3-piece ensuite. The second bedroom features a wall to wall closet, while the third bedroom also enjoys its own walk-in closet. An upgraded 4-piece bathroom serves the additional bedrooms. The finished basement provides a large recreation room with plenty of space for family movie nights, games, a home gym or a comfortable second living area. Step outside to enjoy the backyard, complete with a deck, shed and above-ground pool (seasonal - removed in winter months), offering flexibility for future use of the yard. A great opportunity to enjoy the best of Orangeville living, with the shops, restaurants and amenities of downtown just moments from home. Updates: Shingles 50 yr ('14), Windows in upper floor & living room window (excluding dining and rear door)('16/17'), Main & Upper Laminate Flooring ('21), Furnace, A/C & Heat Pump ('24), Primary Ensuite & Vinyl Flooring ('25), Upper bathroom (except tub/shower)('26), Upper bathroom vinyl plank flooring ('26), Shed ('26).

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New property listed in Orangeville

I have listed a new property at 71 Shirley Street in Orangeville. See details here

Welcome to 71 Shirley Street, a well-appointed detached home in the heart of downtown Orangeville backing onto Myr Morrow Park. Here, everyday convenience meets comfortable family living. Ideally located close to downtown shops, restaurants, parks, schools, trails and local amenities, this 3-bedroom, 3-bathroom home offers a great combination of space and location. The main floor features a large welcoming living room, dining area with French doors walking out to a deck and lovely rear yard, and a functional kitchen! A convenient 2-piece powder room completes the main level. Upstairs, the spacious primary bedroom offers a walk-in closet and updated 3-piece ensuite. The second bedroom features a wall to wall closet, while the third bedroom also enjoys its own walk-in closet. An upgraded 4-piece bathroom serves the additional bedrooms. The finished basement provides a large recreation room with plenty of space for family movie nights, games, a home gym or a comfortable second living area. Step outside to enjoy the backyard, complete with a deck, shed and above-ground pool. The pool can also be disassembled when desired, offering flexibility for future use of the yard. An attached garage adds everyday convenience and additional storage. A great opportunity to enjoy the best of Orangeville living, with the shops, restaurants and amenities of downtown just moments from home. Updates: Shingles 50 yr ('14), Windows in upper floor & living room window (excluding dining and rear door)('16/17'), Main & Upper Laminate Flooring ('21), Furnace, A/C & Heat Pump ('24), Primary Ensuite & Vinyl Flooring ('25), Upper bathroom (except tub/shower)('26), Upper bathroom vinyl plank flooring ('26), Shed ('26).

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I have sold a property at 77 Zina Street in Orangeville

I have sold a property at 77 Zina Street in Orangeville on Sep 30, 2026. See details here

Welcome to 77 Zina Street, a charming bungalow located on one of Orangeville's most sought-after streets, just steps from downtown shops, restaurants, theatres, schools, parks, and everyday amenities. With bright, functional living spaces and a deep backyard, this home offers the perfect blend of comfort and unbeatable in-town convenience. Stepping inside, you're greeted by a sun-filled sunroom featuring oversized windows, and elegant wall sconce lighting - a warm and inviting space to enjoy year-round. The heart of the home is the stylish open-concept kitchen and dining area, complete with quartz countertops, a centre island, ample cabinetry, and a convenient walkout to the oversized fully fenced backyard with a spacious deck and storage shed - ideal for entertaining and outdoor living. The adjoining living room offers an open-concept feel with pot lights and laminate flooring, creating a seamless and comfortable main living space. The main level features three well-appointed bedrooms, each with large windows that bring in an abundance of natural light. A beautifully renovated 4-piece bathroom with ceramic finishes and a ground-level laundry area adds further functionality with a vaulted ceiling, laminate flooring, and a walkout to the garden. Additional living space is found in the partially finished lower level, offering a versatile recreation room perfect for a family room, play area, or home office, along with plenty of storage potential. Set on a deep lot in a highly walkable location close to everything downtown Orangeville has to offer, this home is a fantastic opportunity for families, downsizers, or anyone looking to enjoy the charm and ease of in-town living. Updates: Roof ('15), Furnace ('19) Air Conditioner ('19), Garden Shed ('21), New Front Door ('22) [All As per previous owner]; Rear Door ('24), Deck Rail Added ('26), Portion of new Fence ('26), Painting Throughout ('26)[Current owner]

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What’s Happening This Weekend October 01 - October 04

What’s Happening Around Orangeville: October 01–October 04

Events

Downey’s Farm Pumpkinfest | September 19–October 31

Celebrate fall with Pumpkinfest at Downey’s Farm. Tickets are available online only at DowneysFarm.com.

Orangeville Farmers’ Market | Saturday, October 3, 8 a.m.–1 p.m.
Shop local vendors on 2nd Street at Town Hall.

Dufferin Farm Tour | Saturday, October 3, 9 a.m.–4 p.m.
Explore local farms and agricultural stops throughout Dufferin County.

Pumpkinfest | Saturday, October 3, 12–4 p.m. Hosted by the Rotary Club of Shelburne at Natasha Paterson Memorial Park.

Live Music & Music Nights

Thursday, October 1

GoodLot: Duncan Ivany, 5–7 p.m.
The Hatter: Mark Dorsey, starting at 6:30 p.m.
Broadway Beat: Jam Night, starting at 6:30 p.m.
Bar on Broadway: Karaoke, 7–11 p.m.
Lightcaster: Speed Dating, 6:45–8 p.m., plus Table for Two live acoustic music and Happy Hour, 8–10 p.m.

Friday, October 2
GoodLot: Twilight Troubadours, 4–7 p.m.
Revival 1863: The Music Factory Band.
Broadway Beat: The Earharts, 8 p.m.
The Creek Pub & Eatery: Peace Emett, 7:30–11:30 p.m.
Lightcaster: Magic Friday featuring Andrew Woo, 8–9:15 p.m., followed by DJ until midnight.

Saturday, October 3

GoodLot: The Crawleys, 4–7 p.m.
Revival 1863: The Hit Disturbers.
Broadway Beat: Have A Cigar – Pink Floyd Tribute, 8 p.m.
Lightcaster: Social Saturday Stand-Up Comedy, 8–9:30 p.m.

Sunday, October 4
GoodLot: Onion Honey, 2–5 p.m.
Broadway Beat Bar: Karaoke, 7–11 p.m.
Lightcaster: Progressive Euchre, 12:30–3:30 p.m., followed by Open Mic, 4:30–8:30 p.m.

The Ginny & And’er’son Team
Office: 519-941-5151 | Mobile: 519-938-0028

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I have sold a property at 169 Melissa Crescent in Wellington North

I have sold a property at 169 Melissa Crescent in Wellington North on Sep 22, 2026. See details here

Welcome to 169 Melissa Crescent, a well-maintained raised bungalow offering a functional layout and plenty of living space for families, first-time buyers, or those looking to downsize without compromising on room. With 3+1 bedrooms and 1+1 bathrooms, this home combines comfortable everyday living with a finished lower level that adds valuable flexibility. The bright main floor features a kitchen with tile flooring, and an open-concept layout that flows seamlessly into the dining area. Durable vinyl flooring ('24) extends throughout the remainder of the main level, leading into the sun-filled living room with a large front window. The spacious primary bedroom offers convenient semi-ensuite access to the 3-piece bathroom, while two additional bedrooms each feature ample closet space and large windows. The finished lower level expands your living space with a spacious recreation room featuring an electric fireplace, and walkout to the backyard, creating the perfect setting for entertaining, relaxing, or family movie nights. A fourth bedroom with vinyl flooring, a double closet, and a window provides excellent flexibility for guests, a teenager, or a home office. A convenient 2-piece bathroom completes the lower level. Located in a family-friendly neighbourhood in Mount Forest, this home is close to parks, schools, shopping, and everyday amenities, making it an excellent opportunity to enjoy comfortable small-town living. Updates: Basement Vinyl Flooring ('26), Deck ('25), Shed ('23), Eaves ('25), Main Bath ('23)

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What’s Happening in Orangeville: September 17–20

EVENTS

Orangeville Farmers’ Market Saturday, September 19 | 8 a.m.–1 p.m. Shop fresh local produce, baked goods and artisan products while supporting local farmers and vendors.

Orangeville Oktoberfest Saturday, September 19 | Noon–1 a.m. Mill Street, Downtown Orangeville | Free admission Enjoy a taste of Bavaria with Ontario craft beer, German-inspired food, live entertainment, local shopping and seasonal celebrations.

Oktoberfest Night Market Saturday, September 19 | 3–9 p.m. Mill Street, Downtown Orangeville | Free admission Explore The Hometown Market Night Market featuring local vendors, shopping, food and festive fall fun as part of Orangeville Oktoberfest.

LIVE MUSIC & ENTERTAINMENT

Thursday, September 17

John Cheesman at GoodLot | 5–7 p.m.
Jam Night at Broadway Beat | 6:30 p.m.
Dufferin County Boys at The Hatter | 6:30 p.m.
Latin Dance Night at Lightcaster | 7–10 p.m.
Music Bingo at Tap House | 7–9 p.m.
Karaoke at Bar on Broadway | 7–11 p.m.

Friday, September 18
Rag Maple at GoodLot | 4–7 p.m.
One Row Back at Broadway Beat | 8 p.m.–midnight
Key Legends at Lightcaster | 8 p.m.–midnight
Karaoke with Josh O. at Tap House | 8–11 p.m.

Saturday, September 19

Stoney Lonesome at GoodLot | 4–7 p.m.
Vinyl Countdown at Broadway Beat | 8 p.m.–midnight
Tap House Oktoberfest Bier Garden with craft beer, food and live music

Sunday, September 20

Odd Marshall at GoodLot | 2–5 p.m.
Open Mic at Lightcaster | 4:30–8:30 p.m.
Industry Night Karaoke at Broadway Beat | 7–11 p.m.

The Ginny and ‘er’ son Team Think SOLD – Think Ginny And’er’son
Office: 519-941-5151 Mobile: 519-938-0028

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I have sold a property at 427 Pineview Gardens in Shelburne

I have sold a property at 427 Pineview Gardens in Shelburne on Sep 15, 2026. See details here

Welcome to 427 Pineview Gardens, a charming 3-bedroom, 2-bathroom bungalow in an established neighbourhood in the welcoming community of Shelburne. The main floor offers a comfortable and functional layout, enhanced by large windows that fill the home with natural light and showcase beautiful views of the mature trees surrounding the property. The bright living room features hardwood flooring, a gas fireplace with a wood cabinet surround, and an impressive picture window spanning much of the wall, creating a stunning view of the private setting. A dedicated dining area and well-appointed kitchen with an oversized window and ample cabinetry complete the main living space. The primary bedroom provides a peaceful retreat with a closet, while two additional bedrooms each offer their own closet space and windows. Hardwood flooring throughout all bedrooms ! A 4 pc main bathroom, 2-piece bath and convenient laundry room with storage cabinets and a walkout to the backyard complete the main level. The lower level adds valuable extra living space with a fourth bedroom or office and a large partially finished recreation room, perfect for family hangouts or entertaining. Outside, enjoy the fully fenced backyard, where mature trees create a private and peaceful setting for relaxing, gardening, or spending time with family. A handy storage shed provides additional space for outdoor equipment, while the garage adds everyday convenience. With a practical bungalow layout, beautiful natural views, inviting outdoor space, and plenty of potential to make it your own, this home is a wonderful opportunity just steps from Shelburne's downtown core.

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New property listed in East Luther Grand Valley

I have listed a new property at 17 Deaken Drive in East Luther Grand Valley. See details here

This well-appointed 3+1 bedroom raised bungalow is located in the quaint hamlet of Colbeck, and offers exceptional space both inside and out. The main level features a bright living room with hardwood flooring and a large picture window overlooking the front yard. The layout flows seamlessly into the combined kitchen and dining areas. The kitchen is finished with ceramic flooring, a tiled backsplash, a window above the sink, stainless steel appliances, abundant cabinetry, and a centre island offering additional storage. The dining area, with hardwood flooring, includes a walkout to the two-tiered deck. Three bedrooms are located on the main floor, all with laminate flooring and windows that fill the space with natural light. The primary bedroom includes a walk-in closet and a private 3-piece ensuite. A 5-piece bathroom on the main level provides added convenience for family and guests. The finished lower level opens into a spacious family room with surround sound wiring, a cozy recreation area featuring a fireplace and broadloom, a dedicated laundry space, and a fourth bedroom with broadloom flooring and a window. A full 4-piece bathroom completes the basement, featuring a jacuzzi-style soaker tub, walk-in shower, vanity, window, and ceramic tile finishes. Outdoors, the expansive two-tiered deck is equipped with a retractable canopy and integrated deck lighting, wrapping around the above-ground pool (12' x 26') - perfect for entertaining. The spacious backyard is further enhanced by a full detached 20' x 50' garage/workshop, offering endless possibilities for storage, hobbies, or a home-based workspace. An attached garage and an extended driveway provide ample parking. Updates: Van EE System (2024), Pool Liner (1 yr), Pool Pump (4 yrs), House Garage Door (3 yrs), Washer/Dryer (3 yrs) Submersible Well Pump (6 yrs).

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What’s Happening In & Around Orangeville | September 10–13

There’s lots happening in and around Orangeville this weekend! From the Farmers’ Market and live music to trivia, karaoke and more, here’s your weekend lineup.

LOCAL EVENTS

SATURDAY, SEPTEMBER 12

Orangeville Farmers’ Market – 8AM – Downtown Orangeville, beside Town Hall

Maple Syrup Farm Experience – Elliott Tree Farm – 10:30AM & 12:30PM – Hillsburgh

The Fergus Farm 5th Annual outdoor live music event featuring Orangeville-based Stölen with Lennox & The Hot Flashes. Doors open at 6:30PM, with music from 7:30PM–12AM

LIVE MUSIC & ENTERTAINMENT

THURSDAY, SEPTEMBER 10
Jay Kipps – 5PM – GoodLot
Gary & Scooter – 6:30PM – The Hatter Pub
Jam Night – 7PM – Broadway Beat
Sean O’Grady – 7PM – Lightcaster Orangeville

FRIDAY, SEPTEMBER 11
Lucas Stagg – 4PM – GoodLot
Kenny V. – 8PM – Taphouse
Fifty 50 – 8PM – Lightcaster Orangeville
River Rats – 8PM – Broadway Beat

SATURDAY, SEPTEMBER 12
James Kilby – 4PM – GoodLot
Kenny V. – 4:30PM – Deja Vu Diner
Deux Def Dudes – 8PM – Broadway Beat
After Dark Trivia – 8PM – Lightcaster Orangeville
DJ Dylan – 9PM – Taphouse
Shelburne’s OG Karaoke Night – 9PM – The Dufferin Public House

SUNDAY, SEPTEMBER 13
Stan Chang – 1PM – Taphouse Craft Beer + Kitchen
Traveling Wannabes – 2PM – GoodLot
Open Mic – 4:30PM – Lightcaster Orangeville
Industry Night Karaoke – 7PM – Broadway Beat
Trivia Night – 7PM – Taphouse

The Ginny and ‘er’ son Team
Think SOLD – Think Ginny And’er’son
Office: 519-941-5151
Mobile: 519-938-0028

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