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What's good in Winston Churchill Boulevard tonight?

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What's happening near Winston Churchill Boulevard

Food and drink specials, live events, recurring activities, and nearby business posts from the rolling Winston Churchill Boulevard feed.

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$6.99 plus HST per person for Wednesday night game nights

NEW! Wednesday night game nights here at Active Games Now! Choose from a variety of board games and card games to play with you, your friends and family! Only $6.99 plus HST per person!

Wednesdays · 0.8 km away
Local
Weekly

Wednesday night game nights

NEW! Wednesday night game nights here at Active Games Now! Choose from a variety of board games and card games to play with you, your friends and family! Only $6.99 plus HST per person!

Wednesdays · 0.8 km away
Event

Guided Tour of Gardens and Artworks

Visual Arts Mississauga at Riverwood — Date: Friday, August 28th 2026 Time: 10:00 AM - 1:30 PM

Fri Aug 28 · 7.7 km away
Facebook

$7+HST/Adult for 2 or more children

Playtown — - NEW RATE UPDATE: If booking for 2 or more children, all adults will be $7+HST/Adult.

New Rate Update · 4.5 km away
Local
Event

Blackberry Smoke Headliner Show

Southside shuffle — featuring headliner Blackberry Smoke, proudly presented by Visit Mississauga on September 12, 2026!

Sat Sep 12, 2026 · 7.8 km away
Local
Event

Visit Mississauga Main Stage

Southside Shuffle Blues & Jazz Festival — featuring headliner Blackberry Smoke, proudly presented by Visit Mississauga on September 12, 2026!

Sat Sep 12, 2026 · 8.0 km away
Event

Celebrate Muhammad Annual Mawlid Festival 2026 - Mississauga, ON

Anapilis Halls — Join us for an uplifting evening of Mawlid, nasheeds, scholars and remembrance celebrating our Beloved Prophet Muhammad ﷺ.

Sat Aug 22, 2026 · 7.6 km away
Event

28th Annual Tim Hortons Southside Shuffle Blues & Jazz Festival

Port Credit Memorial Park — Established in 1999. Award-winning blues and jazz festival hosted in the village of Port Credit, Mississauga in Ontario Canada.

Fri Sep 11, 2026 · 7.7 km away
Event

ROOM38 | Before the ROOM | Pilates by the Water

Harding Waterfront Estate — Join us for Pilates by the Water, the first event in ROOM38's Before the ROOM Series—a collection of curated wellness experiences.

Sun Aug 23, 2026 · 2.4 km away
Event

Watercolor Journals

A relaxing watercolor journaling session at the lakeside park.

Sun Aug 9, 2026 · 2.7 km away
Local
Event

HYROX Half Simulation at Sky Fitness

SkyFitness — Test your fitness, pacing, and race strategy before your next HYROX race, or experience the challenge for the first time at Sky Fitness.

Sun Aug 30, 2026 · 4.2 km away
Event

FUNDRAISING TRIVIA NIGHT

Erindale Concessions — ***FUNDRAISING TRIVIA NIGHT*** Day: Friday, 28 August 2026 Time: Starts at 6:30pm Price: $40 per person Location: Ainslie Football Club

Friday, 28 August 2026 · 6.8 km away
Event

After Breast Cancer Pilates by the Water: Candlelight Edition - Mississauga

Richard's Memorial Park — Join us for gentle pilates by the water, specially designed for those after breast cancer.

Sat Aug 15, 2026 · 5.6 km away
Local
Event

After Breast Cancer Yoga by the Water: Candlelight Edition - Mississauga

Richard's Memorial Park — Join us for gentle yoga by the water, specially designed for those after breast cancer.

Sat Aug 15, 2026 · 5.6 km away

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Like the pulse around Winston Churchill Boulevard? See homes near these spots → Ask Scout if Winston Churchill Boulevard fits you

What it's like to live here

Read the neighbourhood like a local: daily errands, green space, housing, and the current pulse around Winston Churchill Boulevard.

Open living guide →
Daily errands23 nearby

Food, coffee, shopping and everyday stops mapped from local business data.

Walkable core29 close-by

Places within roughly a 15-minute walk of the neighbourhood centre.

Green space10 parks & trails

Parks, trails and outdoor stops nearby that shape the week-to-week feel.

Browse homes

What Scout's hearing around the neighbourhood

Extreme Pita Extreme Pita in Oakville offers a fresh Mediterranean-inspired menu with a variety of stuffed pitas, salads, and wraps made with high-quality ingredients.

Around Oakville

Winston Churchill Blvd At Bromsgrove Rd Getting around: Winston Churchill Blvd At Bromsgrove Rd is one of the transit stops serving the area.

Scout's note

Clarkson Park Clarkson Park is the neighbourhood's spot for a walk or some fresh air.

Scout's note

Chefs Door Shawarma Pita and Grill Chefs Door Shawarma Pita and Grill is a go-to local spot for a bite around here.

Scout's note

Updated August 7, 2026

Find your kind of day

Pick a door — each one's a focused guide, no endless scroll.

This Weekend

Weekend picks in Winston Churchill Boulevard

Only dated event listings are shown here; bookable partner offers stay separate and sponsored.

Aug 7-9
Fri Aug 7

Build-A-Bowl

tourismburlington.ca

Build-A-Bowl

Discovered · Dated source feed · Confidence: Strong (source, date, venue)
DetailsSource info

Through the lens

Places in this neighbourhood, as photographed by the people who know it.

Submit your photo →

Get directions Parking · 29 lots Where to stay — of 12 open now

Know this area? Share a local tip · List your business free

The quick read

What is happening in Winston Churchill Boulevard this week?

Winston Churchill Boulevard has 30 current event listings. Current picks include Oakville Latin Social - A Night of Salsa & Bachata!, Stark Naked & The Fleshtones in Oakville (at The Moonshine) SAT AUG 08 - early show 8 pm, Rainbow Loom Bracelet Bash at Staples Store 4.

What can families do in Winston Churchill Boulevard?

Family-coded listings near Winston Churchill Boulevard include Bunny Yoga in Mississauga, North American Pie-Making Class (Hamilton), Introductory Astronomy for Kids - Solar System - SOLD OUT. Check each event page for time, venue, price, parking, and local notes.

Are there free things to do in Winston Churchill Boulevard?

There are 9 event listings that look free or no-cost near Winston Churchill Boulevard, including Oakville Latin Social - A Night of Salsa & Bachata!, Stark Naked & The Fleshtones in Oakville (at The Moonshine) SAT AUG 08 - early show 8 pm, Rainbow Loom Bracelet Bash at Staples Store 4.

What is a good date-night idea in Winston Churchill Boulevard?

For a date night near Winston Churchill Boulevard, start with Chocolatier MasterClass (Hamilton), Fiesta Mexicana: A Culinary Experience, Mirror Glaze Cake Experience (Hamilton), then use the Eat & Drink guide for coffee, dinner, or a nearby stop.

What is Winston Churchill Boulevard good for day to day?

Winston Churchill Boulevard has 2 food and drink places and 5 mapped parks in the current Tiny Local Adventure map, plus current event and local-news signals when available.

What are homes like in Winston Churchill Boulevard right now?

Tiny Local Adventure currently sees 5 home listings in or near Winston Churchill Boulevard, with a median asking price around $959,900.

Is Winston Churchill Boulevard a good place to live?

Winston Churchill Boulevard has 4 parks and green spaces, 2 places to eat, and 21 shops and services mapped within the neighbourhood. There are 6 homes currently for sale here. Use the guide below to judge the day-to-day fit for you.

What are homes like in Winston Churchill Boulevard?

There are 6 homes for sale in and around Winston Churchill Boulevard, priced from $714,900 to $1,699,000 (median about $1,059,000). See the Homes page for current listings.

Good to know

What is there to do in Winston Churchill Boulevard?

Winston Churchill Boulevard has 4 parks and green spaces, 2 places to eat, and landmarks like local landmarks. Use the curated day plan, or jump straight to Eat, Do, Events, Parks, Shop, or Homes.

Where should I park in Winston Churchill Boulevard?

Most of Winston Churchill Boulevard is residential with free street and lot parking near the parks and main streets. See Getting Here for mapped lots.

How do I get to Winston Churchill Boulevard?

Winston Churchill Boulevard sits in Oakville, Ontario, reachable by car, by transit, or by the local trails for cyclists.

Can I see homes for sale in Winston Churchill Boulevard?

Yes — the Homes page lists houses currently for sale in and around Winston Churchill Boulevard, and can connect you with a local agent.