Area Two Cigar Nights are back for 2025! Grab a drink and head up to our rooftop (21+ only) to enjoy.
We’ve partnered with The Owl Shop — Connecticut’s oldest and most premier tobacconist — to offer a hand-selected, rotating selection of high-quality cigars, curated by The Owl Shop to complement our innovative beer lineup. Experience the elevated pairing of bold brews and premium cigars at Two Roads’ newly revived rooftop at Area Two Experimental Brewing. Whether you’re unwinding at sunset or capping off your visit, this rooftop experience blends craftsmanship, flavor, and atmosphere in true Two Roads style.
Every Friday, now through fall, we’re offering guests 20% off all cigars — It’s the perfect opportunity to gather with friends, sip something special, and enjoy a good smoke in great company. Whether you’re a seasoned cigar lover or just exploring, our rooftop is your destination for relaxed, flavorful Fridays.
Here’s what is available weekly:

Recommended Pairings:
- Nub 460 Maduro
Beer Pairing: Espressway Cold Brew Coffee Stout | 6.5%
Why: The bold roasted malt character and coffee/chocolate notes of our Espressway Stout mirror the cigar’s smoked wood and coffee bean flavors, creating a deep, rich pairing with balanced intensity. Both offer complexity and a lingering finish.
- Oliva Connecticut Reserve Robusto
Beer Pairing: No Limits Hefeweizen | 5.0%
Why: Medium-bodied and crisp with subtle sweetness and citrus notes, No Limits Hefeweizen won’t overpower the mild cigar. These beers enhance the Connecticut’s creamy texture and toasted almond notes while refreshing the palate.
- Oliva Serie O Toro
Beer Pairing: Two-Mavé Pivo (Brewery Exclusive) | 5.5%
Why: The Oliva Serie O Toro’s profile featuring leather, roasted nuts, and subtle spice perfectly complements the malt-forward character of a Tmavé Pivo. The cigar has enough richness to stand up to the deep Bohemian malts, while the beer’s crisp, dry finish cleanses the palate, letting the cigar’s complexity shine through. Plus, the slight spiciness from Saaz and Kazbek hops enhances the earthy, nutty notes of the cigar without overwhelming them.
- Upsetter Django by Foundation
Beer Pairing: Blood Peach Lambic (Area Two Exclusive) | 6.7%
Why: This vibrant pairing brings together the sweet-tea and citrus infusion of the Upsetter Django with the tart, fruity brightness of our Blood Peach Lambic. The cigar’s subtle herbal notes and honeyed finish are elevated by the lambic’s lively acidity and ripe peach character, creating a refreshing, aromatic experience that’s both bold and unexpected. A perfect fusion of funk, fruit, and flavor.
- Owl Shop 85th Anniversary Cigar
Beer Pairing: Bourbon Barrel-Aged Cherry Quad | 13.1%
Why: With notes of chocolate, molasses, and coffee, this cigar calls for a beer that can match its richness. Our Belgian-style tripel aged in bourbon barrels, the Bourbon Barrel-Aged Cherry Quad’s warming sweetness and subtle spice echo the cigar’s bold character, while the cherry notes add a lush, fruit-forward contrast.