Castle Rock Holiday Sip & Stroll
By Connor Tien, DougCo Social · Updated July 2026
One night in early December, downtown Castle Rock stays open late. The shops pour something festive, the carriage rides run, and you walk the block with a passport collecting stamps. It's free, and last year it packed downtown in a snowstorm. Here's how it works — and when the next one is expected.
📌 The 2026 date has not been announced yet
It has landed in early December both years it has run — the 2025 edition was Thursday, December 4. That makes Thursday, December 3, 2026 the most likely night. Treat that as expected, not confirmed.
Mod Mountain and the downtown merchants post it as a Facebook event a few weeks out. We'll update this page the day it drops — subscribe and we'll put it in your inbox.
What last year looked like
❄️ And it snowed. The 2025 edition ran on a freezing night right after a fresh snow, and people strolled shop to shop in the cold all evening anyway. About 150 completed passports came back — and that only counts the ones who bothered with the card. Hundreds more were just downtown, shopping on a Thursday night in December.
How the passport crawl works
No sign-up, no ticket. You just show up.
- 1. Grab a passport at any participating shop once the event starts.
- 2. Walk downtown and collect stamps. Each shop stamps your passport, pours a festive sip, and puts out something to eat.
- 3. Turn in a completed passport before the night is over.
- 4. Win a gift card to one of the downtown shops.
How many stamps? It depends on how many shops sign on — the threshold scales with the size of the event. December 2025 was set at six. The summer 2026 edition was set at eight. The 2026 holiday number will be set once the shop list is final.
What the holiday edition has that summer doesn't
- 🐴 Horse and carriage rides — running downtown through the evening. A genuine Castle Rock holiday hallmark, and the thing people remember.
- ✨ The lights — downtown is lit for the season, and the Star is on above town.
- 🍫 The food and drink go up a level — festive mocktails, dirty sodas, hot chocolate and chai, poppy seed bread, peppermint bark, and a frankly dangerous number of cookies.
- 🎁 The deals are real — shops ran free gift with purchase, 10% off storewide, and 25% off select items. It is genuinely a good night to knock out holiday shopping.
Where it came from
This is not a Town event and it is not a Chamber event. It started with one shop, in December 2024.
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. The second one, in December 2025, packed downtown in the snow. It is 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 too.
Who took part in 2025
The lineup changes every edition and gets locked in close to the date. These are the 16 shops from the December 2025 edition, plus the two that joined late — a good guide to who to expect.
On our calendar
The 2026 holiday Sip & Stroll isn't on the calendar yet — it hasn't been announced. It'll appear here automatically the moment it is.
The rest of the season downtown
The Sip & Stroll sits in the best stretch of Castle Rock's year. The Castle Rock Starlighting kicks the season off on Saturday, November 21 — the Saturday before Thanksgiving, not after — when the Star goes on above town and the fireworks follow. The Festival Park Starlight Market runs the same downtown blocks on December 4 and 5. Pair any two of them and you have your holiday shopping done.
Frequently Asked Questions
When is the next Castle Rock Holiday Sip & Stroll?+
The date has not been announced yet. It has landed in early December both years it has run — the 2025 edition was Thursday, December 4 — so early December is the safe assumption, and Thursday, December 3, 2026 is the most likely night. Treat that as expected, not confirmed. Mod Mountain and the downtown merchants post it as a Facebook event a few weeks out, and we will update this page as soon as they do.
What is the Holiday Sip & Stroll?+
A free evening passport crawl through downtown Castle Rock. The shops stay open late, each pouring a festive drink and putting out something to eat, 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. In 2025 it ran from 5 to 8 p.m.
How does the passport work?+
Grab a passport at any participating shop once the event starts — there is no sign-up and no particular place you have to begin. Get a stamp at each stop. Turn in a completed passport before the night is over and you are entered to win. In 2025 you needed six stamps to qualify; the threshold moves with the size of the event, so the more shops that sign on, the more stops it takes.
How much does it cost?+
Nothing. The event is free, 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 point of a holiday shopping event.
What can you win?+
At the December 2025 edition there were fifteen $25 gift cards — one from each participating shop — drawn from the completed passports.
Are the carriage rides part of it?+
Yes, and they are one of the best parts. Horse and carriage rides run downtown during the holiday edition — a genuine Castle Rock holiday hallmark, and something the summer edition does not have.
Is it worth going in the cold?+
Evidently. The 2025 edition ran after a fresh snow, in freezing weather, and people strolled shop to shop all evening anyway. Roughly 150 people turned in a completed passport, and that only counts the ones who bothered with the card — hundreds more were just downtown shopping on a Thursday night.
Who started it?+
Mod Mountain Boutique, in December 2024. 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 run by Mod Mountain together with Downtown Castle Rock, and it has spun off a summer edition.
Where do I find the official details?+
The Facebook event. The Sip & Stroll is a downtown merchants event and it is not listed on the Downtown Castle Rock website, so do not go looking for it there. The final shop lineup and specials get posted in the days beforehand.
Sources: Details of the December 2025 edition — date, time, passport rules, prizes, and the participating-shop list — from our own reporting in the Castle Rock Crew newsletter and the official Facebook event. The 2026 date has not been announced; the early-December expectation is based on the two prior editions, not on an announcement. Check the Facebook event for the final lineup and specials.
We'll tell you the day the date drops
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