Think & Drink: The Complete Guide to Trivia Nights in Ridgefield
Updated May 2026
If you're anything like me, you have a brain full of "useless" information that is just waiting for its moment to shine. Well, Ridgefield is officially a Trivia Town. Whether you want a high-stakes multimedia showdown or a cozy evening with a glass of Syrah, we have got a seat for you. Here is the dirt on where to play, when to go, and who to bring.
A few years ago you would have been hard-pressed to find a trivia night within city limits. Now there are five venues running regular events — on four different nights of the week, across every possible vibe from rowdy sports bar to candlelit winery. The scene has genuinely arrived.
What follows is the most complete guide to trivia in Ridgefield you will find anywhere, organized by night and by venue. Check the quick-reference table at the bottom before you head out, because times and formats can shift — and always confirm on the venue's own events page if you are driving across town.
| Venue | Night | Time | Format | Ages |
|---|---|---|---|---|
| 3Peaks Public House | Tuesday | 7:00 PM | Geeks Who Drink | All ages |
| Ridgefield Craft Brewing | Tuesday | 6:30–8:30 PM | 5 Star Trivia | 21+ |
| Playmakers Sports Bar | Wednesday | 6:30 PM | Themed nights | All ages |
| Taps Beer Reserve | Wednesday | 6:30 PM | Varies / community events | All ages (dog-friendly patio) |
| 14 Acres Vineyard & Winery | Varies | Evening | 5 Star Trivia | 21+ |
Tuesday Trivia
Two very different rooms, same great nightTuesday has quietly become the best trivia night in Ridgefield — largely because you have two genuinely distinct options that do not compete with each other so much as complement each other. One is family-friendly and relaxed; the other is a timed, visual, 21-and-up affair. Both are worth your Tuesday.
The Vibe: Casual and family-friendly. Hosted by Geeks Who Drink in their "Small Batch Trivia" format — shorter rounds, a little more laid-back, and genuinely fun even if you are not a hardcore competitor. This is the place to bring a mixed group where not everyone is in it to win it.
There is plenty of outdoor space (with heaters) and a menu that actually has food for kids, which makes it a rare trivia venue where bringing the whole family is not a logistical headache.
The Vibe: High-energy and visual. RCB uses 5 Star Trivia with PowerPoint rounds, which means you actually have something to look at while you ponder which 80s movie featured that obscure car. Prizes, friendly competition, and craft brews — it is the full package.
This is a popular night and the taproom fills up fast. If you are not there early to claim a table, you are standing.
Pro Tip: Get there early. It is 21+ and it fills up — a barstool is not guaranteed if you show up at start time.
"Whether you want a high-stakes multimedia showdown or a cozy evening with a glass of Syrah, Ridgefield has a seat for you."
The Wednesday Midweek Rumble
Three venues. Three very different experiences.If you survived Tuesday, Wednesday offers three distinct flavors of competition — a loud, TV-packed sports bar, a buzzy taproom with 40 beers on rotation, and a laid-back winery setting that happens to also run great trivia. Pick your vibe.
The Vibe: The Madison Square Garden of Ridgefield trivia. It is loud, there are 60+ TVs, and the energy is electric. They often run themed nights — Disney, Marvel, 90s Pop Culture — so you can actually strategize your team composition ahead of time. This is where the competitive teams come to play.
Pro Tip: This place books out. If you have a team of six, call ahead — or you will be watching from the parking lot.
The Vibe: Social and buzzy. Taps often partners with local groups — fitness clubs, community organizations — to fold trivia into a community event rather than just a bar night. The rotating tap list of around 40 beers gives you something to discover while you think.
The dog-friendly patio is a genuine differentiator. If you have a four-legged team member, this is their venue.
Trivia with a View: 14 Acres Vineyard & Winery
The most relaxed room in townIf the sports bar energy is not your thing but you still want to show off that your brain is full of useful facts, 14 Acres is your answer. This is trivia at a different pace — glass of Syrah in hand, estate views in the background, and Five Star Trivia keeping things competitive without the noise.
The Vibe: Relaxed, scenic, and surprisingly competitive. 14 Acres runs a recurring Five Star Trivia series on evenings throughout the year — and the stakes are fun: each night's winner takes home a free bottle of wine. The estate setting on NE 244th Street makes this the most scenic trivia room in the area by a wide margin.
This is the place to bring people who are maybe not die-hard trivia players but would genuinely enjoy an evening out. The combination of good wine, good company, and a quiz is a reliable crowd-pleaser.
Pro Tip: Dates vary — check the 14 Acres events page before you plan your night. The series runs throughout the year but is not weekly.
General Tips for Ridgefield Trivia Nights
- Teams of four to six tend to be the sweet spot — broad enough knowledge base, small enough that everyone contributes.
- Confirm times directly with the venue before heading out, especially around holidays when schedules shift.
- If you are going to Playmakers on a Wednesday, call ahead. It fills up faster than any other venue on this list.
- Ridgefield Craft Brewing and 14 Acres both use 5 Star Trivia — if you like one, you will probably like the other.
- Geeks Who Drink (3Peaks) have a slightly different scoring system than 5 Star — no wrong-answer penalty, which keeps things fun even for casual players.
Ridgefield's trivia scene has grown faster than almost anyone predicted, and it is still growing. If a new venue starts running a regular night — or an existing one changes their schedule — we will keep this guide updated. Got a tip? Let us know.
Know of a trivia night we missed? Tell us about it.
