The Cigars Worth Smoking in the First Week of Fall
Why the First Week of Fall Is the Best Time to Light Up
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There is something about the shift into September and October that makes a premium cigar feel more earned. Temperatures drop just enough to slow down a long smoke, the humidity stabilizes in most of the country, and the season itself carries a certain deliberate quality — shorter days, longer evenings, the smell of leaves in the air. Fall also happens to align with when tobacco aged through the summer is at its most expressive, which means the sticks you pull from your humidor right now are often at their peak. The 11 cigars that follow span a range of body, origin, and price point, but each one earns its place in the rotation when the calendar finally turns.
Padrón 1964 Anniversary Maduro: Nicaragua's Autumn Standard
Few cigars belong to fall the way this one does. The 1964 Anniversary Series was launched in 1994 to mark Padrón's 30th anniversary, and its sharply box-pressed shape ignited a trend across the entire cigar industry. The Maduro expression wraps aged Nicaraguan long-filler in a dark, oily wrapper and delivers a flavor profile of coffee bean, cocoa, earth, and hazelnut — notes that read like a dessert menu for cool-weather evenings. Each cigar is aged four years before release, earning it a 95-point rating and the number one Cigar of the Year title in 2021. It is a medium-to-full-bodied smoke with flawless construction and an even burn that holds up through a long, unhurried session. Buy it now!
Liga Privada No. 9: The Broadleaf Bully Worth Every Minute
Jonathan Drew's Liga Privada No. 9 was originally blended for the private consumption of Drew Estate's master blenders before demand forced it into wider — though still limited — production. The star of the construction is the jet-black Connecticut Broadleaf wrapper, fermented all the way to Oscuro, which is toothy, oily, and carries an immediate sweetness before you even light it. Underneath sits a Brazilian Mata Fina binder and a long-filler blend of Nicaraguan and Honduran tobaccos sourced from seven different farms. The smoke delivers deep notes of dark chocolate, espresso, sweet tobacco, and earth, with a complex retrohale that most cigars simply cannot match. It earned a 94-point score and a spot in Cigar Aficionado's Top 25 list, and it remains one of the most complete full-bodied smokes ever made in Nicaragua. Buy it now!
My Father The Judge: Cigar of the Year and Built for the Season
My Father The Judge won Cigar Aficionado's Cigar of the Year for 2024 — the third such title for the Garcia family, widely considered one of the most celebrated cigar-making dynasties working today. The blend starts with an oily Ecuador Sumatra wrapper over well-aged Nicaraguan long-filler tobaccos grown across Estelí, Jalapa, and Namanji, three of Nicaragua's most prized growing valleys. Its flavor profile is rich and layered — woody notes of leather, cedar, earth, and pepper build toward a nutty, toasty finish that lingers long after the last draw. At a full body with carefully controlled strength, it rewards attention without punishing the smoker. If you are going to smoke one new-ish release in the first days of fall, this is the one to reach for. Buy it now!
Alec Bradley Prensado Churchill: Honduras Proved the World Wrong
The Prensado was Cigar Aficionado's Cigar of the Year in 2011 and remains the only Honduran cigar to hold that title. Creator Alan Rubin built it around a supremely aged Honduran Corojo wrapper leaf sourced from the Trojes region of southern Honduras — a leaf he deliberately held in extended fermentation at the Raices Cubanas factory rather than using it in an earlier project. The filler is a complex combination of aged Honduran and Nicaraguan tobaccos, and the result opens with a blast of pepper and subtle mesquite sweetness before settling into rich notes of leather, coffee, and dried fruit. In the final third it paradoxically becomes smoother rather than harsher, finishing with a creamy, chocolatey elegance. The Churchill vitola earned a 96-point rating, making it the format of choice for a slow fall evening. Buy it now!
Oliva Serie V Melanio: Ecuador's Finest Wrapper, Nicaragua's Heart
The Serie V Melanio was created as a tribute to Melanio Oliva, the family patriarch who first grew tobacco in Cuba before relocating to Nicaragua, and it shows the accumulated knowledge of four generations of growers. The cigar wears a silky Ecuador Habano Sun Grown wrapper — one of the most photogenic in the industry — over a Nicaraguan binder and filler from the Jalapa and Estelí valleys. Flavor-wise, expect a bold and spicy profile of dark chocolate, red pepper, coffee, and a creamy sweetness that softens the strength in the final third. Multiple sizes have earned 95-point scores from Cigar Aficionado, and the Figurado in particular is considered a benchmark for the Ecuadorian wrapper category. Its complexity and burn quality make it an excellent choice when you want something substantial but not overwhelming for a weekday evening smoke. Buy it now!
Joya de Nicaragua Antaño 1970: The Original Nicaraguan Powerhouse
Joya de Nicaragua holds the distinction of being the country's oldest premium cigar factory, and the Antaño 1970 is its most legendary full-strength expression. Rolled using a ligero-heavy selection of all-Nicaraguan tobaccos, the 1970 is unusually smooth in delivering its bold hallmark flavors of leather, spice, earth, and cocoa — a combination that earned it a 92-point score from Cigar Aficionado. The blend is a direct reference to Joya's founding year, and smoking it carries a sense of historical weight that few Nicaraguan cigars can claim. It is an unapologetically full-bodied smoke, best suited to experienced aficionados who want strength with genuine complexity rather than brute force alone. Pair it with a smoky Scotch or a bold espresso when the temperature finally drops into the low 60s. Buy it now!
Casa Turrent Serie 1973 Torpedo: Mexico's Answer to Full-Flavored Fall Smoking
The Casa Turrent Serie 1973 Torpedo is one of the more interesting full-flavored smokes in the premium market, and one of the few that puts Mexican tobacco front and center across the entire blend. The wrapper, binder, and most of the filler are San Andrés tobacco grown on the Turrent family's farms in the San Andrés Valley of Mexico, with a small amount of Nicaraguan filler rounding out the core. Cigar Aficionado awarded it 93 points, noting its chubby semi-pressed figurado format packs the tobacco dense enough to sustain flavors of dark earth, leather, cocoa, and a distinctly Mexican sweetness across the full smoke. The Turrent family has been farming in San Andrés since 1880, giving them one of the longest continuous lineages in the New World cigar industry. It is a welcome departure from the Nicaragua-or-nothing mindset and one of the most underrated picks for a long fall session.
Perdomo Habano Bourbon Barrel-Aged Maduro: Fall's Most Literal Pairing
Nick Perdomo's Habano Bourbon Barrel-Aged line takes a concept that sounds gimmicky and executes it with the kind of seriousness that Perdomo brings to every blend he releases. The tobaccos spend time aging inside genuine bourbon barrels, which impart a subtle sweetness and vanilla warmth to the underlying Nicaraguan filler before the cigars are finished with a dark, oily Maduro wrapper. The resulting smoke layers cocoa, leather, toasted oak, and a gentle bourbon sweetness into a medium-to-full profile that transitions beautifully across the three thirds. Construction is meticulous — Perdomo grows much of his own tobacco in Nicaragua's Estelí and Jalapa regions, giving him rare farm-to-cigar control over quality. For a cigar that self-consciously evokes autumn's signature flavors, this one earns the right to lean into the season. Buy it now!
Rocky Patel Vintage 1990: Aged Tobacco, Effortless Complexity
Rocky Patel launched the Vintage 1990 as a showcase for what genuinely aged tobacco can do to a blend — the Honduran and Nicaraguan fillers inside were aged for roughly a decade before rolling, producing a smoke of unusual smoothness for its medium-to-full strength. The cigar is wrapped in a Sumatra seed Ecuador wrapper that adds a light, slightly sweet counterbalance to the depth of the aged interior tobaccos, and the combination produces notes of cinnamon, cedar, earth, and a long, creamy finish. It is one of the most approachable entry points into Rocky Patel's premium tier for smokers who want genuine complexity without the aggression of a full-bodied Nicaraguan puro. The construction is reliably excellent across vitolas, making it a smart choice when you want a dependable, no-drama smoke that still rewards focused attention. On a cool September evening, the Toro is the format to reach for. Buy it now!
Davidoff Winston Churchill The Late Hour: When the Night Gets Serious
Davidoff's Winston Churchill line was designed around the sensory world of Britain's most famous cigar smoker, and The Late Hour expression is its most immersive interpretation — built explicitly for the quieter, darker hours of the evening. Blended by Davidoff's team using tobaccos from the Dominican Republic under an oily Ecuadorian Sun Grown wrapper, The Late Hour is a fuller, richer departure from the original Churchill blend, with tasting notes of dark dried fruits, roasted oak, leather, and rich cocoa moving through a well-constructed medium-to-full body. It earned consistent 90-plus scores from the major rating publications and is produced at Davidoff's own Dominican factory, ensuring construction quality that rarely disappoints. The concept of the late hour — fire in the fireplace, whiskey poured, the day finally over — maps perfectly onto the first week of fall. Pair it with a peated Scotch or a long-aged bourbon for full effect. Buy it now!
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