EVENTS
We host some awesome events throughout the year in Downtown Littleton. Whether it's a business or the community, Littleton always has something to do!
Introducing a Brand-New Event
Introducing a brand-new event in Downtown Littleton! The Downtown Littleton Wine Walks, brought to you by the Littleton Merchants Association, invite you to sip, stroll, and experience the heart of our community in a whole new way.
Stroll through participating businesses, enjoy curated wine tastings, and explore everything our vibrant downtown has to offer.
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Sip, Stroll, and Discover
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Event Details
Dates: Final Friday of each month, May – September
Time: 4:30 PM – 7:30 PM
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2026 Dates:
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May 29
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June 26
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July 31
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August 28
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September 25
Tickets:
$30 per person in advance. $35 day of
(Includes wine tastings at participating locations + event glass)
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TICKET LINK COMING SOON
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How It Works
Check In:
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Start your evening at the designated check-in location (soon to be announced). You’ll receive your wine glass, wristband, and event map.
Sip & Stroll:
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Visit participating businesses throughout downtown and enjoy wine tastings at each stop.
Explore:
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Shop, dine, and discover new favorites while experiencing Downtown Littleton in a lively, social setting.
Participating Businesses​
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Juniperseed Mercantile
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Bridgets Botanicals with Creative Grace in Montion
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​J Claire Women's Fashion
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Lollygag Antiques & Boutique
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ElseWear Collective
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True Find Boutique
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Savory Spice
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Uptown County & Boutique
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Central Bank
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Five Wellbeing Spa
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Creative Spaces
Check back as our list continues to grow!
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Sponsorship Opportunities
Promote your business and support one of Downtown Littleton’s most exciting new events.
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Multiple sponsorship levels available
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Exposure to hundreds of attendees each month
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Opportunities for on-site engagement
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Annual Events
Block Party
Saturday, June 13th, 2026
5:30 pm - 10:30 pm
Experience Downtown Littleton's charm at the Annual Littleton Main Street Block Party in June. It's a community celebration with a circus theme featuring local food, beverages, merchants, music and much more!
Check out the website HERE
Littleton Restaurant Week
September 11th - 20th, 2026
During this 10 day celebration restaurants and bars showcase their talents with food and drink specials.
Click HERE for participating restaurants
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Farmer's Market
2026 Dates Coming Soon
Support local and get your fill of fruits and veggies at the Downtown Littleton Farmers Market on Nevada St. north of Main St.
Chalk Art
2026 Date Coming Soon
Watch local artists create their masterpieces on the sidewalks of Main Street in Downtown Littleton.
Bring the kiddos!
Artists start at 8 am
​Follow @walk_the_chalk_littleton on Instagram for more information
Illuminate Littleton
Friday, July 24, 2026
6-10pm
Littleton has been selected by the Colorado Tourism Office as a host city for a statewide 150th anniversary drone show. This is a significant honor and a rare opportunity to showcase Littleton on a regional and statewide stage.
To celebrate this milestone event, Main Street will transform into an open-air experience with illuminated and interactive art installations, roaming musical performances, and extended outdoor dining from local restaurants and bars. Inviting residents and visitors to explore, linger, and connect before the evening culminates in a spectacular drone show lighting up the Littleton sky.
Click HERE for more info​
Western Welcome Week
August 7 - 16, 2026
August 15th: Grand Parade and Annual Craft Fair in Downtown Littleton
This annual August celebration begins on Friday and continues for nine days. Saturday's Festival Day includes the Littleton Firefighters Children's Parade, Grand Parade, annual Arts & Crafts Fair and concessions by local civic groups. WesternWelcomeWeek.org
Pumpkin Poles
Halloween begins with the creation of Pumpkin Poles by the downtown
merchants. They will be on display in early October through Halloween
(depending on the condition of the pumpkins). Located throughout
downtown on Main, Alamo and Prince Streets, visit early in the month.
You don't want to miss these one-of-a-kind creations.
Goblin Give Out
Sunday, October 25th, 2026
a beloved annual Halloween tradition in Downtown Littleton that invites families to celebrate the season in a fun, safe, and community-focused way. Children are encouraged to wear costumes and trick-or-treat at participating local shops and restaurants, where merchants hand out candy throughout the afternoon. The event brings the community together while supporting small businesses and creating festive fall memories for families across downtown
Candlelight Walk
Friday, November 27th, 2026
This Littleton tradition is a festive evening of holiday lights and music for
the whole family. Sip hot cider, listen to holiday music and see reindeer!
Donations of non-perishable food for Inter-Faith Community Services are
accepted during the evening as well as toys for the Arapahoe Santa
Claus Shop. Main Street merchants stay open late for those who want to
start their holiday shopping.
Small Business Saturday
Saturday, November 28th, 2026
LOCAL IS GOOD! This day encourages people to shop at small
businesses on the Saturday after Thanksgiving. The single day has grown into a powerful movement and more people are taking part than ever
before.