Say goodbye to summer the Colorado way—surrounded by mountains, music, and unbeatable deals. On Sunday, August 31, 2025, Cooper Creek Square in Winter Park is throwing its annual Labor Day Block Party & Sidewalk Sales, and it’s the perfect excuse to spend your long weekend in the fresh alpine air.
From bargain hunters to live music fans, foodies to families with toddlers in tow, this all-day event is designed for everyone who wants to make the most of the final stretch of summer. Whether you’re a local, a visitor, or just passing through, the Labor Day Block Party promises fun, flavor, and a few can’t-miss markdowns.
End-of-Season Energy in the Heart of Winter Park
There’s something undeniably magical about Labor Day weekend in the Rockies. The air starts to turn crisp, the wildflowers make their final curtain call, and the community comes together for one last sun-drenched celebration before autumn begins to peek around the corner.
Cooper Creek Square, a favorite local shopping and dining hub, transforms into a lively pedestrian playground on Sunday. You’ll find open-air stalls, sale racks, and sidewalk displays with major markdowns from boutique shops, outdoor outfitters, and local artisans. It’s one of the best times all year to snag unique finds at a steal—whether you’re looking for a cozy new sweater, mountain-inspired decor, or early holiday gifts.
A Party You Can Feel Good About
What makes the Labor Day Block Party more than just a shopping spree is the atmosphere. This isn’t just retail therapy. It’s a celebration of local businesses, community connection, and Colorado’s famous mountain hospitality.
Expect live music filling the square, kids laughing as they run through bubble machines or chalk up the sidewalks, and dogs (on leash, of course) sniffing out new friends. Many shops offer snacks, giveaways, or small surprises at checkout. It’s the kind of event where you start off casually browsing and end up spending hours simply enjoying yourself.
And did we mention the free parking? It’s as low-stress as mountain events get.
Family-Friendly and Pet-Approved
Yes, this event is pet-friendly, and yes, it’s absolutely great for kids. Bring the whole crew. There’s space to spread out, benches for relaxing, and plenty of options to grab food and drinks without leaving the action. Parents can shop while the kids play nearby, and four-legged friends are welcome to wag along for the fun.
It’s the kind of event where you’ll see grandparents sipping coffee in the shade while teenagers compare their sidewalk-sale hauls and younger kids devour a cone from a nearby sweet shop.
Everyone belongs here. That’s part of what makes it special.
Fuel Up While You Shop
Shopping on an empty stomach? Not at this block party. Cooper Creek Square is home to a variety of local eateries serving up everything from wood-fired pizzas to gourmet sandwiches, international cuisine, and Colorado-style comfort food.
Whether you’re grabbing a casual bite on a sunny patio or sitting down for a celebratory dinner after a long day of scoring deals, there’s a table waiting with your name on it.
And yes, there’s coffee. And ice cream. And maybe even a well-earned margarita if you’re ready to toast the weekend in style.
Make It a Weekend Worth Remembering
Labor Day isn’t just a day off—it’s a chance to reset before the seasons shift. Why not stretch the fun into a full weekend escape?
Winter Park is brimming with opportunities for late-summer adventure: hike or bike a scenic trail, catch a concert, enjoy a gondola ride, or just soak up the mountain sunshine. And when the party wraps up at Cooper Creek Square, there’s still plenty to explore.
Unwind in Style at The Jabberwocky
When the sun sets and your shopping bags are full, retreat to The Jabberwocky, Winter Park’s coziest place to stay. Located just a few minutes from the heart of town, it’s the perfect landing spot for Labor Day weekend adventurers.
At The Jabberwocky, you’ll find:
- Thoughtfully designed rooms that feel like a retreat
- Quiet, relaxing surroundings just off the main buzz of downtown
- Easy access to the block party, restaurants, trails, and more
- The kind of comfort that helps you truly unwind—without ever feeling far from the action
It’s where mountain-town charm meets well-earned rest. And yes, your shopping bags will fit just fine.
One Day. One Square. One Perfect Send-Off for Summer.
Don’t miss the chance to celebrate the end of summer with the best of Winter Park. The Labor Day Block Party & Sidewalk Sales is a little bit retail therapy, a little bit community pride, and a whole lot of mountain fun.
Bring your friends. Bring the dog. Bring an extra tote bag—you’ll need it.
And when you’ve had your fill of food, fun, and festival magic, make your way to The Jabberwocky, where the pillows are plush, the pace is peaceful, and your Colorado summer ends exactly how it should: warm, relaxed, and a little bit sun-kissed.
Let Labor Day be more than a Monday off. Let it be your perfect mountain memory.
