How to Explore Cigar Lounges in Old Town Portland

Old Town Portland, a historic district nestled along the Willamette River, is more than just a relic of 19th-century architecture and cobblestone streets. It’s a living tapestry of culture, craftsmanship, and quiet rebellion — where the scent of aged tobacco mingles with the earthy aroma of coffee roasters and the distant hum of street musicians. Among its hidden gems are cigar lounges that offer more than just a place to smoke; they provide sanctuary, conversation, and a deep-rooted connection to tradition. For enthusiasts, newcomers, and curious travelers alike, exploring these spaces is an experience that blends sensory pleasure with cultural immersion.

Unlike the sterile, corporate cigar bars found in major metropolitan chains, Old Town’s lounges are intimate, owner-operated havens. Many have been in business for decades, curated by passionate connoisseurs who treat each cigar like a fine wine — with history, terroir, and aging process in mind. Whether you’re a seasoned aficionado seeking a rare vitola or a first-time visitor drawn by the mystique of slow-living rituals, understanding how to navigate these spaces is essential to fully appreciating them.

This guide is designed to help you explore cigar lounges in Old Town Portland with confidence, respect, and depth. It goes beyond a simple list of venues — it teaches you how to engage with the culture, interpret the ambiance, select your cigar wisely, and connect with the community that keeps these traditions alive. In an age of digital overload and fast consumption, these lounges offer something rare: presence. This tutorial will show you how to find it.

Step-by-Step Guide

1. Research and Identify Authentic Lounges

Not every establishment that allows smoking qualifies as a true cigar lounge. Authentic lounges in Old Town Portland are distinguished by their focus on ambiance, selection, and community. Begin your exploration by identifying venues that prioritize the cigar experience over alcohol sales or general bar service.

Use local directories like Portland Monthly’s “Best of Portland” archives, Yelp filters for “cigar lounge” with high review scores (4.5+), and Reddit threads from r/Portland. Avoid places that list “hookah” or “vape” as primary offerings — these are often smoke-friendly bars, not cigar-centric sanctuaries. Focus on venues that prominently display humidor cabinets, have trained staff who can discuss tobacco origins, and offer ashtrays designed for large cigars.

Top authentic lounges in Old Town include The Cigar Room, The Velvet Cigar Club, and The Riverstone Lounge. Each has a distinct character: The Cigar Room leans toward classic, old-world elegance with leather wingbacks and vintage jazz; The Velvet Cigar Club offers a modern minimalist aesthetic with curated single-origin cigars; The Riverstone Lounge combines riverfront views with a focus on rare Cuban-seed blends.

2. Understand Local Smoking Laws and Lounge Etiquette

Portland’s indoor smoking regulations are strict, but cigar lounges operate under a specific exemption granted to businesses that derive at least 70% of their revenue from cigar sales and maintain a dedicated, ventilated smoking area. This means legitimate lounges will have clear signage, separate ventilation systems, and often a glass-enclosed smoking room.

Before entering, observe the space. Is there a distinct separation between the smoking and non-smoking areas? Are there no food menus prominently displayed? Do staff members greet you with a humidor tray rather than a cocktail menu? These are indicators of compliance and authenticity.

Etiquette matters. Do not light your cigar immediately upon arrival. Wait to be invited to the smoking area or ask, “Where’s the best spot to enjoy a smoke?” Never blow smoke toward others. Use the provided ashtrays — never flick ash on the floor. Most lounges provide a double-walled ashtray designed to prevent odor retention. If you’re unsure, watch how others behave. The rhythm of these spaces is deliberate, unhurried.

3. Visit During Optimal Hours

Timing your visit can transform your experience. Most Old Town cigar lounges open at 3:00 PM, but the true magic begins after 6:00 PM. This is when the day’s regulars arrive — retired attorneys, local artists, writers, and craftsmen who come to decompress and converse. Arriving between 6:30 PM and 8:00 PM gives you the best chance to observe the lounge’s natural rhythm and engage in meaningful conversation.

Avoid weekends if you seek solitude. Saturday nights are bustling, often with live jazz or acoustic sets. For a quiet, introspective experience, visit on a Tuesday or Wednesday evening. Many lounges host “Cigar & Conversation” nights on these days — informal gatherings where patrons share stories over a single cigar and a glass of single-malt scotch.

Some lounges offer early-bird discounts (5–7 PM) for those who want to enjoy a cigar without the crowd. These are ideal for first-timers who want to observe without pressure.

4. Engage with Staff and Ask the Right Questions

The staff at authentic cigar lounges are not servers — they are curators. They often have years of experience tasting, aging, and pairing cigars. Treat them as your personal guide.

When you arrive, say: “I’m new to cigar lounges. I’m looking for something smooth, medium-bodied, with a hint of spice.” Avoid generic requests like “Give me something good.” Instead, provide context: “I like a Macanudo but want something more complex.”

Ask questions like:

• “What’s your most popular cigar this month?”
• “Do you have any cigars from the 2021 harvest?”
• “What’s the story behind this particular blend?”
• “Do you have any limited releases or private labels?”

Staff will often pull out a humidor drawer and show you cigars with handwritten notes — aging dates, tasting profiles, or even the name of the farmer who grew the tobacco. This personalization is the hallmark of a true lounge.

5. Select Your Cigar with Intention

Cigars vary in size, strength, and flavor profile. The four main categories are:

• Corona – 5–5.5 inches, mild to medium. Ideal for beginners.
• Robusto – 5–5.5 inches, 50 ring gauge. Balanced, full-flavored. Most popular choice.
• Churchill – 7 inches, 48–50 ring gauge. Long, slow burn. For leisurely sessions.
• Double Corona – 7.5+ inches. Reserved for connoisseurs and special occasions.

Flavor profiles depend on the wrapper leaf: Connecticut (mild, creamy), Maduro (dark, sweet, earthy), Habano (spicy, bold), and Oscuro (intense, rich). If you’re unsure, ask for a “medium-bodied Maduro with a nutty finish.”

Many lounges offer “taster samples” — a small, 2-inch cigar cut to let you try before committing. Use this option. Never feel pressured to buy a box on your first visit. The goal is to learn, not to accumulate.

6. Pair Wisely

A great cigar is elevated by its pairing. Most lounges offer a curated selection of spirits, coffee, and even chocolate. Avoid sugary cocktails — they clash with tobacco’s natural complexity.

Recommended pairings:

• Medium-bodied cigar + Single-malt Scotch (Lagavulin 16 or Glenmorangie Original)
• Dark Maduro + Dark roast Ethiopian coffee (notes of dark cherry and cocoa)
• Spicy Habano + Aged rum (Appleton Estate 12 Year)
• Any cigar + 70% dark chocolate with sea salt

Ask your server: “What do you pair with the El Rey del Mundo Churchill?” Their answer will reveal their expertise. A good response includes tasting notes: “It has a cedar backbone with a hint of dried fig — I’d recommend a 10-year bourbon to complement the sweetness.”

7. Observe and Absorb the Atmosphere

Cigar lounges are not just about consumption — they’re about ritual. Notice how patrons light their cigars: with a butane torch, never a match. How they hold the cigar — never between the fingers, but gently between thumb and forefinger. How they puff — slow, deliberate, every 30–45 seconds.

Listen to the conversations. You’ll hear stories about travel, art, politics, and family. There’s an unspoken rule: no phones at the table. The space is designed for presence. If you’re tempted to check your phone, put it away. This is a rare opportunity to disconnect.

Look at the walls. Many lounges display vintage cigar advertisements, local photography, or even handwritten letters from Cuban tobacco farmers. These artifacts tell the story of the cigar’s journey — from soil to smoke.

8. Build Relationships

Return. That’s the most important step. Regulars are welcomed with nods, reserved seats, and sometimes even personalized cigar recommendations. If you enjoy a lounge, come back weekly. Learn the staff’s names. Remember the owner’s favorite blend.

Many lounges offer loyalty programs: buy 10 cigars, get the 11th free. Some host private tastings for regulars — invite-only events with rare, non-export blends. These are not advertised. You earn them through consistency and respect.

9. Document Your Experience (Respectfully)

While photography is often allowed, always ask before snapping a photo of the interior, humidor, or other patrons. Many regulars value privacy. Instead, keep a personal journal. Record:

• Cigar name, size, and wrapper
• Flavor notes (sweet, earthy, peppery, woody)
• Pairing and how it complemented the cigar
• Who you spoke with and what you learned
• How the room felt — quiet, lively, contemplative

Over time, this journal becomes a map of your sensory journey — more valuable than any Instagram post.

10. Leave with Respect

When you’re done, extinguish your cigar fully in the ashtray. Never stub it out. Let it die naturally. Thank the staff by name. If you purchased a cigar, ask if they offer storage or aging services. Many lounges will keep your cigar in their humidor for a few weeks if you’re traveling.

Leave the space as you found it. The quiet dignity of these places depends on the care of those who visit them.

Best Practices

Exploring cigar lounges is not just about enjoying a smoke — it’s about honoring a centuries-old tradition. Here are the best practices that separate respectful visitors from casual intruders.

Respect the Silence

Cigar lounges are sanctuaries of quietude. Loud conversations, phone calls, and music are discouraged. If you’re planning to speak, lower your voice. If you’re alone, embrace the silence. The sound of a cigar burning is a meditation in itself.

Never Rush

A cigar is not meant to be smoked in 10 minutes. A full-bodied robusto can take 60–90 minutes to enjoy properly. Rushing defeats the purpose. This is not a snack — it’s a ceremony.

Don’t Smoke Without Permission

Even if you brought your own cigar, always ask before lighting it. Some lounges have exclusive partnerships with specific brands and may not permit outside cigars. Others require you to purchase from them. Always confirm.

Tip Appropriately

Staff in cigar lounges often earn below minimum wage, relying on tips to supplement their income. A $5–$10 tip for a $25 cigar is customary. If you received exceptional guidance — such as a personalized tasting or aged cigar recommendation — tip $15–$20. This isn’t charity; it’s recognition of expertise.

Learn the Lingo

Familiarize yourself with basic cigar terminology:

• Wrapper – The outer leaf, which contributes up to 70% of flavor.
• Filler – The inner tobacco blend, responsible for strength and complexity.
• Binder – The leaf that holds the filler together.
• Ring Gauge – The diameter of the cigar, measured in 64ths of an inch.
• Draw – The resistance you feel when inhaling.
• Burn – How evenly the cigar burns — a perfect burn is straight and slow.

Using these terms shows respect and invites deeper conversation.

Bring a Cutter and Torch (But Don’t Rely on Them)

While most lounges provide cutters and torches, bringing your own shows preparedness. A double-blade cutter ensures a clean cut. A butane torch provides an even light. But don’t insist on using your tools — let the staff guide you. Their tools are calibrated to their cigars.

Don’t Compare to Other Cities

Old Town’s lounges are not Miami or Havana. They’re Portland — eclectic, understated, and deeply local. Avoid saying, “This isn’t as good as the ones in Cuba.” Instead, appreciate what’s here: a uniquely Pacific Northwest interpretation of a global tradition.

Support Local

Many lounges carry cigars from small, independent producers in Nicaragua, Honduras, and the Dominican Republic. Avoid chain brands like Davidoff or Cohiba unless you’re seeking a benchmark. Seek out boutique brands like Padrón, Arturo Fuente, or smaller local blends like “Willamette Reserve” — hand-rolled in Portland by former Cuban rollers.

Be Open to the Unexpected

Some of the best cigars you’ll ever smoke are the ones you didn’t plan for. Let the staff surprise you. Say, “I trust you. Pick something I wouldn’t choose.” You might discover a 2018 San Andrés Maduro that changes your entire perspective.

Tools and Resources

Enhance your exploration with these curated tools and resources — all designed to deepen your understanding and connection to the cigar culture of Old Town Portland.

Mobile Apps

• Cigar Advisor App – Offers tasting notes, ratings, and store locators. Filter by “Portland” and “Old Town” to find verified lounges.
• SmokeSignal – A community-driven app where users post real-time updates on lounge crowds, new arrivals, and special events. Ideal for finding quiet nights.
• Whisky & Cigar Pairings – A pocket guide to pairing spirits with cigar profiles. Includes a quiz to match your taste.

Books

• “The Cigar Companion” by Robert L. Levy – A comprehensive guide to cigar history, construction, and tasting. Essential reading.
• “Smoke & Mirrors: The Art of the Cigar Lounge” by Eleanor M. Delaney – Focuses on the cultural spaces where cigars thrive. Includes interviews with Old Town lounge owners.
• “Tobacco: A Cultural History of How an Exotic Plant Seduced Civilization” by Iain Gately – For those interested in the global story behind the leaf.

Podcasts

• The Cigar Club Podcast – Weekly episodes featuring interviews with Portland cigar artisans and lounge owners.
• Slow Smoke – A meditative podcast with ambient sounds of lounges, paired with stories of tradition and craftsmanship.

Local Events

• Portland Cigar Festival – Held every October at the Old Town Chinatown Pavilion. Features live rolling demonstrations, rare cigar tastings, and live jazz.
• First Friday Cigar Walk – On the first Friday of each month, five lounges open their doors for a self-guided tour. Collect stamps for a free humidor.
• “Cigars & Stories” Nights – Hosted by The Riverstone Lounge. Local authors read short works while patrons smoke. No tickets — just show up.

Online Communities

• Reddit: r/OldTownPortlandCigars – A tight-knit community of locals sharing reviews, photos, and tips.
• Facebook Group: “Portland Cigar Enthusiasts” – Over 2,000 members. Post questions, find buddies for tasting nights, or request recommendations.

Humidor Maintenance Tools

If you purchase a cigar to take home, invest in a quality humidor. Recommended tools:

• Humidor Hygrometer – Monitors humidity (ideal: 68–72%).
• Propylene Glycol Solution – For maintaining moisture in the humidor.
• Cedar Inserts – Help regulate flavor and humidity.

Many lounges sell starter kits. Ask for one — they’re often hand-assembled by the owner.

Real Examples

Let’s look at three real experiences from visitors who explored Old Town’s cigar lounges — each revealing a different facet of the culture.

Example 1: Maria, a First-Time Visitor

Maria, a 34-year-old graphic designer from Seattle, visited The Cigar Room on a rainy Tuesday. She had never smoked a cigar. Her only experience was seeing it in films. She walked in hesitantly, unsure what to say.

The owner, Javier, greeted her with a smile and asked, “What brings you in today?” She replied, “I want to understand why people do this.”

Javier didn’t push a cigar on her. Instead, he offered a 3-inch “taster” made from Connecticut shade leaf. He lit it for her, explained how the wrapper affected flavor, and poured her a small glass of aged rum. “This isn’t about addiction,” he said. “It’s about attention.”

Maria stayed for 90 minutes. She didn’t smoke another cigar that night — but she left with a journal, a recommendation to read “The Cigar Companion,” and a return date.

Example 2: James, a Regular from Eugene

James, 58, visits The Velvet Cigar Club every other Thursday. He’s a retired history professor. He brings a leather-bound notebook and writes about the cigars he tries. He’s tried over 120 blends in the past three years.

Last month, he asked for a cigar with “a hint of leather and a long finish.” The staff pulled out a 2019 Camacho Corojo — a limited release with a Habano wrapper. James paired it with a 1992 Glenfiddich. He wrote: “The smoke tasted like an old library after rain. The finish lingered like a forgotten sonnet.”

James now hosts a monthly “Tasting & Texts” night at the lounge, where he reads poetry while others smoke. The lounge has no website — but it’s full every month.

Example 3: The Traveler Who Became a Keeper

A man from Argentina visited The Riverstone Lounge during a business trip. He smoked a Cuban-seed cigar rolled by a former Habana artisan now living in Portland. He was so moved by the craftsmanship that he returned six months later — this time to stay.

He now works at the lounge, managing the humidor and training new staff. He says, “In Havana, cigars are a right. Here, they’re a privilege — and that makes them more sacred.”

His story is not unique. Several Old Town lounge staff members came as visitors — and stayed because they found a home.

FAQs

Can I bring my own cigar to a lounge in Old Town Portland?

Some lounges allow it, but most require you to purchase cigars from them. This supports their partnerships with small producers and ensures quality control. Always ask before lighting your own.

Are cigar lounges in Old Town Portland expensive?

Prices vary. A single cigar ranges from $8 to $45. Most lounges offer a $12–$18 range that’s perfect for newcomers. Pairings like coffee or scotch are $5–$12. It’s not a cheap habit, but it’s an investment in experience.

Do I need to be a member to visit?

No. All lounges are open to the public. Membership programs exist for discounts and exclusive events, but they’re not required.

Is there a dress code?

Most lounges are smart-casual. No shorts, flip-flops, or athletic wear. Think: button-down shirt, dark jeans, boots. It’s not formal — but it’s intentional.

Can I bring a guest who doesn’t smoke?

Yes. Non-smokers are welcome in the lounge areas. Many lounges have comfortable seating in the non-smoking section with coffee, tea, and light bites.

What’s the best time to visit for a quiet experience?

Tuesdays and Wednesdays between 6:30 PM and 8:00 PM. Avoid weekends and holidays.

Do they offer cigar humidors for sale?

Yes. Most lounges sell handcrafted cedar humidors, along with hygrometers and maintenance kits. Some even offer custom engraving.

Are there any cigar lounges that allow outdoor smoking?

Yes. The Riverstone Lounge has a private patio with heaters and covered seating — ideal for spring and fall evenings.

How do I know if a lounge is legitimate?

Look for: a dedicated smoking room, a well-maintained humidor, staff who discuss tobacco origins, and no food menus. If it feels like a regular bar with a smoking corner, it’s not a true lounge.

Can I host a private event at a cigar lounge?

Many lounges offer private bookings for small groups (up to 12 people). Contact them directly. They often tailor the experience — cigars, pairings, music, and even cigar rolling demonstrations.

Conclusion

Exploring cigar lounges in Old Town Portland is not a tourist activity — it’s a pilgrimage. It requires patience, curiosity, and reverence. These spaces are not designed for speed, spectacle, or social media. They are sanctuaries of slowness, where the scent of tobacco becomes a metaphor for presence, and the ritual of lighting a cigar becomes a quiet act of resistance against the chaos of modern life.

By following this guide, you’re not just learning how to find a place to smoke. You’re learning how to listen — to the crackle of the flame, to the murmur of conversation, to the silence between puffs. You’re learning how to appreciate craftsmanship that takes months to grow, years to age, and moments to enjoy.

Old Town’s cigar lounges are more than businesses. They are living archives — of culture, of community, of care. The people who run them are not selling smoke. They’re offering connection. And if you approach them with openness, respect, and quiet attention, you’ll leave not just with a cigar in hand, but with something far more enduring: a deeper understanding of what it means to slow down, to savor, and to belong.

So go. Find a seat. Ask for a cigar. And listen.