If you’re in Portland and looking to either pick up a solid cigar or find a spot to kick back with one, you’re in luck. The city may be known for its craft beer and coffee, but it’s also quietly home to some excellent cigar-friendly shops and lounges. I spent the past few weekends poking around, talking to staff and fellow aficionados–so whether you’re a seasoned smoker or just curious about trying something new, this list will point you toward some of the best places in town. Let’s dive in.
1. Windy City Cigars
Windy City Cigars has been around since 2002, serving smokers who want quality tobacco and cigars without unnecessary fuss. It’s an online shop where customers can find everything from pipe tobacco and cigars to rolling papers, cigarette tubes, and smoking accessories. The store has a reputation for keeping things simple – a wide selection, fair prices, and quick shipping. People in Portland who prefer ordering online can easily get their products delivered directly to their door.
Key Highlights:
- Large selection of cigars, pipe tobacco, and accessories
- Online ordering with delivery to Portland
- Frequent deals and discounts
- Fast shipping and easy customer support
Who Will Love This Place:
- Smokers who prefer buying online
- People looking for affordable cigar and pipe tobacco options
- Those who want reliable delivery and simple ordering
Contact Information:
- Website: windycitycigars.com
- Address: 912 Donata Ct,Lake Zurich, IL 60047
- Phone: (866) 233-8796
- Email: support@windycitycigars.com
- Facebook: www.facebook.com/windycitycigars.usa
- Instagram: www.instagram.com/windy_city_cigars
2. Rich’s Cigar Store
Rich’s Cigar Store is one of Portland’s oldest tobacco shops, operating for more than a century. It’s known for its wide range of cigars, pipes, and pipe tobacco, along with a selection of magazines and accessories. The shop still feels old-school in the best way – people come here not just to buy cigars but to talk, browse, and learn from staff who know their blends inside out. Rich’s has two locations in Portland, each offering a relaxed atmosphere and a connection to the city’s cigar community.
Key Highlights:
- Established local business with a long history in Portland
- Large walk-in humidor and pipe tobacco selection
- Two Portland locations with lounges
- Staff knowledgeable about cigars and pipe tobacco
Who Will Love This Place:
- Long-time cigar smokers who appreciate tradition
- People who like personal service and in-person browsing
- Anyone looking for a quiet local spot to relax with a cigar
3. Broadway Cigars
Broadway Cigars is a local Portland lounge and retail shop with multiple locations, including one right on NE Broadway. The shop features large walk-in humidors filled with a variety of cigar brands, and its lounges are set up for comfort with leather chairs, TVs, Wi-Fi, and complimentary drinks. It’s a place where people stop by after work or on weekends to relax, talk cigars, and unwind. They also host events for the cigar community, which gives the place a friendly, social vibe.
Key Highlights:
- Walk-in humidors with a wide cigar selection
- Comfortable lounges with Wi-Fi and free drinks
- Regular community events and cigar tastings
- Two Oregon locations including Portland
Who Will Love This Place:
- Cigar fans who like relaxing in a lounge
- People who enjoy social cigar events
- Those who want a casual, local place to smoke and meet others
4. Cascade Cigar & Tobacco
Cascade Cigar & Tobacco is a well-known spot for cigar and pipe enthusiasts near Portland. The shop has a 1,200-square-foot walk-in humidor stocked with both familiar brands and smaller boutique cigars. Alongside cigars, there’s also a wide variety of pipes and pipe tobacco blends, many mixed in-store. Customers can sit down in the smoking lounge after buying cigars and enjoy the relaxed setup with free Wi-Fi. For anyone outside the area, orders can also be shipped directly to Portland.
Key Highlights:
- Large walk-in humidor with diverse cigar brands
- Smoking lounge with Wi-Fi access
- Hand-mixed pipe tobacco blends available in-store
- Online ordering and delivery to Portland
Who Will Love This Place:
- Cigar smokers who enjoy browsing large humidors
- People who like to relax and smoke indoors
- Those who appreciate smaller, boutique cigar brands
5. Tobacco Town
Tobacco Town runs several locations across Portland and nearby Milwaukie. Each shop keeps a wide range of smoking products, from premium cigars to cigarettes, e-liquids, and accessories. There’s also a selection of beer and wine available, with large walk-in coolers for browsing. Cigars are kept properly humidified, and customers can expect an easy-going shopping experience whether they’re restocking supplies or looking for something new.
Key Highlights:
- Multiple locations in Portland and Milwaukie
- Premium cigars, cigarettes, and e-liquids
- Walk-in coolers for beer and wine
- Casual, straightforward atmosphere
Who Will Love This Place:
- Smokers who like one-stop shops for supplies
- People who enjoy exploring different cigar and tobacco options
- Those who prefer quick, in-person purchases
6. Paul’s Cigars
Paul’s Cigars is a family-run business that’s been part of the Portland and Vancouver area for decades. The shop has multiple locations, including one in Beaverton, and focuses on cigars, pipe tobacco, and accessories. It’s a low-key spot where regulars often drop by to pick up their favorites or try something new from the shelves. Staff are known for being approachable and keeping the stores welcoming and organized.
Key Highlights:
- Family-owned cigar shop with several Oregon and Washington locations
- Good mix of cigars and pipe tobacco
- Comfortable, friendly atmosphere
- Long history of serving the local community
Who Will Love This Place:
- Smokers who prefer small, local shops
- People looking for a familiar place to buy cigars
- Those who value friendly service over formality
7. Tradesmen Cigar Company
Tradesmen Cigar Company is an online cigar brand with national delivery, including to Portland. The brand’s focus is on cigars that reflect traditional craftsmanship, often described as everyday smokes for hardworking people. Their collection includes several lines such as Executive, Journeyman, and Apprentice, along with other Doumitt cigars. The cigars are available online and in select shops, including a few around the Portland area.
Key Highlights:
- Independent cigar company with nationwide shipping
- Several signature cigar lines
- Available online and at partner retailers near Portland
- Simple, practical approach to cigar craftsmanship
Who Will Love This Place:
- Cigar smokers who like ordering online
- Fans of American-made cigar brands
- People who prefer straightforward, quality cigars without extra frills
8. Releaf Cigars
Releaf Cigars operates online and ships across the country, including to Portland. The store sells a range of cigars from well-known brands and offers frequent deals and promotions for repeat customers. The site is simple to use, with clear product categories and quick checkout. It’s a good option for anyone who prefers ordering cigars and accessories online without dealing with store visits.
Key Highlights:
- Online cigar store with delivery to Portland
- Simple ordering and fast checkout
- Frequent online deals for regular customers
- Free shipping on qualifying orders
Who Will Love This Place:
- Shoppers who prefer online convenience
- Portland residents looking for delivery options
- People who like to explore different cigar brands from home
9. Pearl Specialty Market & Spirits
Pearl Specialty Market & Spirits is located in Portland’s Pearl District and combines a liquor store with a cigar selection. The shop carries premium spirits, craft beer, and wine alongside cigars, mixers, and barware. It’s set up more like a curated market than a typical tobacco store, with a focus on variety and presentation. Customers often come here to find cigars that pair well with whiskey or small-batch bourbon. Staff are known for being approachable and helpful, offering simple suggestions when needed. Orders can also be placed for delivery within Portland through platforms like Grubhub or Instacart.
Key Highlights:
- Cigar and spirits shop in Portland’s Pearl District
- Offers cigars, liquor, wine, and accessories in one place
- Knowledgeable staff and relaxed atmosphere
- Local delivery available through Grubhub and Instacart
Who Will Love This Place:
- People who enjoy pairing cigars with whiskey or wine
- Shoppers who prefer a clean, organized store with good variety
- Those who want to order cigars and drinks for delivery in Portland
10. JR Cigars
JR Cigars is a long-standing online cigar retailer that’s been around since the 1970s. The store ships nationwide, including to Portland, and offers one of the largest selections of cigars and accessories online. Customers can find brands like Montecristo, Romeo y Julieta, Padron, and Drew Estate, along with samplers, humidors, and lighters. The website is organized for easy browsing, and delivery is quick with a focus on keeping cigars fresh. There’s also a loyalty program that rewards repeat customers with points and discounts.
Key Highlights:
- Online cigar retailer with delivery to Portland
- Wide range of premium and budget cigar brands
- Accessories like humidors and cutters available
- Loyalty program for returning customers
Who Will Love This Place:
- Cigar smokers who prefer shopping online
- Those looking for variety in brands and accessories
- Customers who like reward programs and regular deals
11. Best Cigar Prices
Best Cigar Prices operates as an online cigar retailer based in Pennsylvania, shipping nationwide including to Portland. The shop is known for its broad selection of brands, ranging from well-known names like Arturo Fuente and Macanudo to smaller boutique labels. Customers can also find samplers, accessories, humidors, and cigar gifts. The website is simple to use and includes regular discounts and clearance options. Orders are shipped from a large climate-controlled warehouse to keep cigars fresh during transit.
Key Highlights:
- Online cigar shop with delivery available to Portland
- Large variety of cigar brands and accessories
- Frequent deals and discounted samplers
- Cigars shipped from a temperature-controlled warehouse
Who Will Love This Place:
- Smokers who buy cigars online regularly
- Customers looking for both premium and affordable cigar options
- People who like exploring new cigar brands without buying full boxes
12. United Cigars
United Cigars has been around since the early 1900s, supplying cigar shops and retailers across the country with blends made in factories throughout the Dominican Republic, Honduras, Nicaragua, and Costa Rica. The company isn’t based in Portland, but anyone in the area can easily order its cigars online through partnered retailers. The catalog covers both high-end and everyday options, from long-established labels like Byron and Atabey to more recent lines such as Firecracker and Abuelo. Each cigar range offers a slightly different experience, whether someone prefers mild, balanced flavors or a stronger, more complex smoke.
The brand’s focus is on keeping traditional cigar-making alive while offering blends that appeal to modern tastes. It’s the kind of supplier that helps fill the shelves of many independent cigar shops, giving customers in places like Portland access to a wide range of exclusive cigars that aren’t easy to find elsewhere.
Key Highlights:
- Cigar manufacturer and distributor established in 1901
- Offers blends produced in major cigar regions across Central America
- Mix of ultra-premium and accessible cigar lines
- Online availability for Portland buyers through retail partners
Who Will Love This Place:
- Cigar enthusiasts looking for brands with history and craftsmanship
- Smokers who enjoy trying different regional blends
- Retailers and customers searching for cigars that aren’t available everywhere
Conclusion
Finding a good cigar shop in Portland isn’t hard, but finding one that feels right for you takes a little exploring. Each place here has its own rhythm – some lean old-school with the smell of aged tobacco and wood counters, others feel more like hangouts where you can settle in for an hour and forget about your to-do list. The nice thing is, Portland doesn’t try too hard about it. Whether you’re picking up a quick smoke, spending a quiet afternoon in a lounge, or getting a box shipped straight to your door, the city covers all kinds of cigar habits.
What stands out most is the mix of tradition and local character. A spot like Rich’s carries a century of history, while Broadway and Cascade bring a more relaxed, modern lounge vibe. Even the online shops that deliver here keep things simple – no fuss, just fresh cigars when you want them. In the end, it’s less about where you buy and more about taking a moment to enjoy it. Portland gets that balance just right.