Castle Rock Sip & Stroll: The Complete Guide
By Connor Tien, DougCo Social · Updated July 2026
One night, one passport, and a whole downtown staying open late. The Sip & Stroll is the best free evening Castle Rock throws — shops pour a drink, put out something to eat, and run specials you will not find any other night. The summer edition is Thursday, July 16, from 5 to 8 p.m., and the holiday edition comes back in December. Here is how it works.
The essentials
How the passport crawl works
There is no sign-up and no ticket. You just show up.
- 1. Grab a passport at any participating shop once the event starts. You do not have to start anywhere in particular.
- 2. Walk downtown and collect stamps. Each shop stamps your passport, pours you a complimentary sip, and puts out something to snack on. Most run a special just for the night.
- 3. Hit 8 or more businesses for the summer edition, then turn your completed passport in before the night is over to get entered.
- 4. Win a gift card. Winners are drawn from the completed passports — gift cards to the participating shops.
The stamp threshold moves with the size of the event — the more shops that sign on, the more stops it takes to qualify. December 2025 was set at six. The July 2026 summer edition is set at eight.
Where it came from
The Sip & Stroll is not a Town event and it is not a Chamber event. It started with one shop.
The team at Mod Mountain Boutique came up with a simple but great idea: what if downtown shops stayed open late for one night, offered a few festive sips and snacks, and made holiday shopping feel like a stroll with friends instead of a chore? That's how the Castle Rock Sip & Stroll was born.
It worked. It has since grown into a downtown-wide event — now run by Mod Mountain together with Downtown Castle Rock — and it has outgrown the holidays entirely, which is why there is now a summer edition.
The holiday edition
❄️ It packed downtown in a snowstorm. The 2025 holiday Sip & Stroll ran on Thursday, December 4 — and it had just snowed and was freezing out. People strolled shop to shop in the cold all evening anyway. Roughly 150 completed passports came back, and that only counts the people who bothered with the card. Hundreds more were just downtown shopping on a Thursday night.
The holiday version is the original, and it is the one worth planning around. Downtown is lit up, there are horse and carriage rides running — a genuine Castle Rock holiday hallmark — and the shops go all in: festive mocktails, dirty sodas, hot chocolate and chai, poppy seed bread, peppermint bark, and a frankly dangerous number of cookies. The deals are real too, with shops running free gift with purchase, 10% off storewide, and 25% off select items.
In 2025 it ran 5 to 8 p.m., free, with six stamps to qualify and fifteen $25 gift cards up for grabs — one from each shop.
📌 The 2026 holiday date has not been announced. It has landed in early December both years (2025 was Thursday, December 4), and it tends to get posted as a Facebook event a few weeks out. We will update this page the moment it drops — subscribe and we will put it in your inbox.
Who takes part
The lineup changes every edition and gets locked in close to the date. These are the shops that took part in the December 2025 holiday edition — a good guide to who to expect. The summer edition has grown past 20 businesses.
The final list of participating shops and their specials gets announced on the Facebook event in the days before. Note that the Sip & Stroll is a downtown merchants event — it is not listed on the Downtown Castle Rock website.
Sip & Stroll on our calendar
Live from our events calendar — updates automatically as new editions get posted.
Make a night of it
The Sip & Stroll is three hours on a weeknight, so it pairs well. On July 16, the same evening, Tunes for Trails has That Eighties Band at the Philip S. Miller Park Amphitheater from 6:30 p.m., and Wide Awake Eatery has a comedy show at 7 p.m. — a short walk from the stroll.
In December, the holiday edition sits in the middle of Castle Rock's best stretch of the year — the Castle Rock Starlighting kicks the season off, and the Festival Park Starlight Market runs the same downtown blocks that same week.
Frequently Asked Questions
What is the Castle Rock Sip & Stroll?+
It is a free evening passport crawl through downtown Castle Rock. Participating shops stay open late, each pouring a complimentary sip and putting out a snack, and most run a special you will not find any other night. You pick up a passport, walk shop to shop collecting stamps, and turn in a completed passport for a shot at a gift card. It started as a holiday shopping event and now runs a summer edition too.
When is the next Sip & Stroll?+
The summer edition is Thursday, July 16, 2026, from 5 to 8 p.m. in downtown Castle Rock. It is free to attend, with more than 20 downtown businesses taking part. The holiday edition typically lands in early December — the 2025 edition was Thursday, December 4 — but the 2026 holiday date has not been announced yet.
How does the passport work?+
Grab a Sip & Stroll passport at any participating shop once the event starts — you do not need to sign up in advance or pick it up anywhere specific. Get a stamp at each stop you visit. For the July 16 summer edition, you need stamps from 8 or more businesses to qualify. Turn the completed passport in before the night ends and you are entered to win a gift card to one of the participating shops.
How much does it cost?+
Nothing. The Sip & Stroll is free to attend, the passport is free, and the sips and snacks at each stop are complimentary. You only spend money if you decide to buy something — which is, of course, the whole idea.
What can you win?+
Gift cards to the participating downtown shops, drawn from the completed passports. The summer edition is giving away several $20 gift cards. At the December 2025 holiday edition there were fifteen $25 gift cards, one from each participating shop.
Who started the Sip & Stroll?+
Mod Mountain Boutique. The idea was simple: what if downtown shops stayed open late for one night, offered a few festive sips and snacks, and made holiday shopping feel like a stroll with friends instead of a chore? It has since grown into a downtown-wide event, now hosted by Mod Mountain Boutique together with Downtown Castle Rock.
Is it worth going?+
The December 2025 edition packed downtown even though it had just snowed and was freezing — people strolling shop to shop in the cold all evening. Roughly 150 people turned in a completed passport, and that only counts the ones who bothered with the card. A summer evening with no snow should be an easier sell.
Where do I park?+
Downtown Castle Rock has free public parking, including the Encore garage on Wilcox and street parking throughout downtown. The event runs on foot along the downtown blocks, so park once and walk. Arrive closer to 5 p.m. if you want the easier spots.
Where do I find the official event details?+
The Sip & Stroll lives on Facebook — it is run by the downtown merchants and Mod Mountain Boutique, and it is not listed on the Downtown Castle Rock website. Follow the Facebook event for the final shop lineup and specials, which get announced in the days beforehand.
Sources: Dates, times, passport rules, and prizes confirmed with the organizers and against the official Facebook events for the December 2025 and July 2026 editions. Attendance and participating-shop details from our own reporting in the Castle Rock Crew newsletter. Last updated July 2026 — the shop lineup and specials are announced close to the date, so check the Facebook event before you go.
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