By The Fletcher Team & Associates
Monument has a lot going for it — the mountain views, the ponderosa pines, the close-knit community feel — and its after-work scene is quietly keeping pace with everything else that makes this town special. Whether you're looking for craft beer, curated wine, or a cold cocktail with a great atmosphere, the best happy hour spots in Monument are worth knowing about. Here's where locals like to land when the workday is done.
Key Takeaways
- A pour-your-own taproom experience that makes every visit feel different
- A wine bar in the heart of historic downtown that's worth every minute of the drive
- A neighborhood sports bar with a loyal local following and solid drink specials
- Cozy spots that combine great food and drinks in Monument's most walkable areas
Trails End Tavern
Trails End Tavern is a self-pour taproom in the heart of downtown Monument with a rotating selection that keeps regulars coming back to see what's new on the wall. The format is simple: grab a tap card, pour what you want, and pay for exactly what you drink.
Why Trails End Stands Out for Happy Hour
- A constantly rotating tap selection that includes local and regional craft options
- A relaxed, low-key atmosphere that works equally well solo or with a group
- Downtown Monument's walkable setting, close to the historic Second Street corridor
- Outdoor space that's particularly enjoyable during Monument's mild summer evenings
The community energy here is genuine — this is the kind of place where you run into neighbors and end up staying longer than you planned.
Cloud Wine
Cloud Wine is one of Monument's most beloved recent additions — a wine-focused bar with a tapas menu that punches well above its small-town surroundings. With a cozy interior, a thoughtful wine list, and small plates designed for sharing, it's an ideal weeknight stop.
What Makes Cloud Wine Worth a Visit
- An impressive wine selection curated for variety and quality, not just volume
- Creative tapas, including dishes like papas bravas, shishito peppers, and bruschetta
- A warm, stylish atmosphere with a water feature that adds to the mountain ambience
- Proximity to The Bistro on 2nd, making it easy to turn a happy hour into a full evening
Cloud Wine opens at 3 PM Tuesday through Saturday, making it a natural first stop before dinner anywhere on Washington Street.
The Bistro on 2nd
The Bistro on 2nd is Monument's most acclaimed dinner destination — but it also serves as an excellent cocktail stop in the early evening before tables fill up. The cocktail program is polished, and the atmosphere is intimate without feeling stiff.
Reasons to Stop by The Bistro on 2nd Before Dinner
- Well-crafted cocktails and a wine list that complements the kitchen's elevated approach
- A warm, intimate setting across two floors in a historic downtown building
- Small bites like bacon-wrapped dates that are ideal for pairing with an early drink
- A vibe that transitions seamlessly from happy hour to a full dinner reservation
Reservations fill up quickly on weekends, so arriving early for drinks is a smart move that often turns into dinner staying well into the evening.
Goat Patch Brewing Company
Goat Patch Brewing's Monument location brings the credentials of one of Colorado's most respected craft breweries to the Tri-Lakes area. The taproom is comfortable, dog-friendly on the patio, and consistently well-stocked with Goat Patch's range of German-style lagers, IPAs, and seasonal releases.
What Keeps Locals Coming Back to Goat Patch
- A well-rounded beer menu anchored by Goat Patch's flagship German-style offerings
- A relaxed taproom with both indoor and outdoor seating options
- Food options that pair well with the beer, including popular pretzel bites
- A welcoming atmosphere that's equally good for a quick pint or a longer hang
For craft beer enthusiasts, Goat Patch Monument is one of the most reliable stops in the area — the kind of place you bring out-of-town guests without any hesitation.
Back East Bar & Grill and Local Landing
For those who prefer a classic bar-and-grill atmosphere, Monument has two strong options worth knowing. Back East Bar & Grill is a well-established sports bar with a broad draft selection, solid pub food, and a loyal following among Monument residents. Local Landing brings a distinctly Colorado vibe with an extended happy hour running from 11 AM to 6 PM, great wings, and an atmosphere reviewers consistently describe as clean, fun, and welcoming.
What These Two Spots Offer Happy Hour Visitors
- Back East's extensive draft beer list and consistent sports bar energy for game-day crowds
- Local Landing's long happy hour window that works well for afternoon stops
- Pub food at both locations that's crowd-pleasing and reasonably priced
- Neighborhood regulars and a genuine local feel that national chains can't replicate
Between the two, you've got solid options whether you're looking for a lively sports atmosphere or a more laid-back neighborhood bar with a Colorado character all its own.
FAQs
What is the best area in Monument for a happy hour crawl?
Downtown Monument along Second Street and Washington Street is your best bet — Cloud Wine and The Bistro on 2nd are within walking distance of each other, and Trails End Tavern is just around the corner on Front Street. You can easily hit two or three spots in an evening without moving your car.
Are Monument's happy hour spots dog-friendly?
Several are. Goat Patch Brewing's Monument location is dog-friendly on the patio, and Trails End Tavern is known for its welcoming atmosphere for four-legged regulars as well. Always worth calling ahead to confirm seasonal outdoor access.
What's the best happy hour option for someone who doesn't drink beer?
Cloud Wine and The Bistro on 2nd are both excellent choices — both offer strong wine and cocktail programs in comfortable settings that don't revolve around the beer tap.
Explore Everything Monument Has to Offer
At The Fletcher Team & Associates, we work with buyers and sellers all across the Colorado Springs area, and part of what we love about this work is helping people truly land in the right community — not just the right house. We know Monument well, and we're committed to making sure every client feels confident and clear about the decision they're making. Real estate is genuinely our passion, and we take real pride in making the process feel straightforward rather than stressful. Whether you're curious about what life looks like here or you're ready to make a move, we'd love to be on your side.
Connect with The Fletcher Team & Associates today.
