The best bars & nightlife in Monroe County

Sango Kura is Pennsylvania's first and only sake brewery, tucked in Delaware Water Gap, pouring house-made sake alongside classic izakaya plates that hit that umami sweet spot. Perfect for a midweek change-up from the usual pint, and yes, everything on the menu plays nice with their brews.

From the East Stroudsburg newsletter, October 20, 2026

For a laid back, family owned spot for pub classics plus legit seafood and steaks, Sycamore Grille hits the weeknight sweet spot. Expect nightly specials, regular live music, and a friendly bar that feels more neighborly than noisy.

From the East Stroudsburg newsletter, October 18, 2026

Tolino Vineyards Stroudsburg pours their Pennsylvania wines right in town, with tastings that make choosing a bottle pleasantly difficult. Swing by for casual indoor or outdoor hangs, custom labels for gift-worthy bottles, and yes, you can stamp your Pocono Beverage Trail card...

From the Stroudsburg newsletter, October 13, 2026

Finola's Irish Pub is an Irish owned hangout locals hit for Guinness, smoked cocktails, and weekly rituals like Taco & Trivia or BBQ Night. The real hook is the stage, with state of the art sound and steady live music that actually feels like a concert.

From the Stroudsburg newsletter, October 17, 2026

RAW Urban Winery & Hard Cidery is the Pocono Mountains’ first urban winery and hard cidery, pouring Napa-style wines, craft small-batch ciders, and coffee from its Organic Coffee Bar. Vegan and gluten free sips keep the whole crew happy when you want a quick Stroudsburg tasting-room hang.

From the Stroudsburg newsletter, October 28, 2026

Family-owned and genuinely local, Happy Hour Bar and Grill pairs signature drinks with a weekly pasta night that nods to its roots, plus a cozy patio that becomes a summer concert hangout. They also cater on and off site, support community events like Stroud Fest, and make regulars feel like family.

From the Stroudsburg newsletter, October 10, 2026

The Warrior Bar & Grill is the local standby where an American grill menu hits the spot, live music keeps nights lively, and TVs seem to multiply during big games. Perfect for rallying the crew after work or posting up for a full slate.

From the East Stroudsburg newsletter, October 10, 2026

The Hideaway Speakeasy is tucked away at Newberry’s Yard of Ale, mixing vintage-leaning cocktails with local flair in a cozy speakeasy nook that’s made for conversation. When you’re craving a proper old fashioned and a little mystery, this is where Stroudsburg hides its best sips.

From the East Stroudsburg newsletter, October 9, 2026

Stonehaüs Meadery & Cidery is a veteran owned Stroudsburg hangout serving mead (aka honey wine) and cider, ideal when beer fatigue hits. Easygoing vibe, friendly pours, and the kind of sips that make weeknights feel like weekends.

From the Stroudsburg newsletter, October 5, 2026

If your bar cart needs a hometown upgrade, Silverback Distillery, an internationally awarded distillery, pours cocktail flights, barrel smoked cocktails, and neat pours in the Pocono region, all crafted by Master Distiller Christine Riggleman.

From the East Stroudsburg newsletter, October 5, 2026

Derailed Taphouse keeps things lively with 32 ever-rotating drafts, a cocktail list that actually tries, and even Napa wine on tap. Pair it with seasonal, upscale comfort food from Executive Chef Dwayne Stewart, then stick around for live music and trivia nights when you want a low-key local hang.

From the East Stroudsburg newsletter, October 11, 2026

Rotating draft lineup, over 100 bottles, and cover-free live music make Flood's the kind of low-key spot you slide into after work and somehow close down. Solid pub grub, drink specials most nights, and a friendly downtown Stroudsburg vibe that never tries too hard.

From the Stroudsburg newsletter, October 3, 2026

Signature Saloon keeps Stroudsburg’s boots tapping with country-themed nights, live bands, and plenty of reasons to sing along. Grab a pint, some legit comfort food, and hit trivia, line dancing or karaoke... it’s the kind of local spot where you’ll probably run into someone you know.

From the Stroudsburg newsletter, October 29, 2026

Trackside Grill & Bar turns the old Dansbury Depot into a lively, TV-filled home base for burgers, wings with house-made sauces, and other pub favorites with a few smart twists. Grab a cold one, catch the game, and let the crowd energy do the rest.

From the East Stroudsburg newsletter, October 27, 2026

Settled into the renovated Stroud farmhouse at Glen Brook Golf Club, The Rusty Putter Bar & Grill serves comfort-food standbys like burgers, wings, fries, and cheesesteaks with six brews on tap, a welcoming vibe, and community-minded events that make it feel like your off-course home.

From the Stroudsburg newsletter, October 24, 2026

When you want a grown-up hang that feels both swanky and comfortable, Puros Cigar Lounge pairs top shelf cigars with proper cocktails, plus a full Rare & Rye Steakhouse menu. Easy spot to catch the game, trade stories, and make Thursday feel like Saturday.

From the East Stroudsburg newsletter, October 14, 2026

Pocono Mountains’ first urban winery and hard cidery, Rowan Asher Winery (RAW Winery) pours Napa-style wines and craft small-batch ciders, with vegan and gluten free options. Think labels like “Sweet Gypsy” or “Pocono Mule,” a Stroudsburg tasting room, and an organic coffee bar when you need a reset.

From the Stroudsburg newsletter, October 25, 2026

Rudy's Tavern keeps East Stroudsburg's classic bar vibe alive with dark wood, checkered floors, arcade games, and reliably cold beer on every day that ends in Y. Go for the Rudy's Super, Cajun Chicken, or a Super Dog, stay for the game, neighbors, and community-first heart dating to 1933.

From the East Stroudsburg newsletter, October 25, 2026

The Cinder Inn is the kind of East Stroudsburg staple where wings and French onion hit the spot, Fridays bring seafood boil, and drink flights keep the table debating favorites. Planning a get-together? Their Ivy Room and Cinder Caterers make hosting easy, right down to servers and boozy buckets.

From the East Stroudsburg newsletter, October 22, 2026

Craving a spot that feels local but never stale? The Goat on Main is a fresh take on the neighborhood corner bar with not-your-ordinary bar bites, a solid beer and cocktail lineup, and weekly happenings like karaoke, trivia with Kyle, Bring Your Own Vinyl, plus live shows, costume parties, and movie nights.

From the Stroudsburg newsletter, October 23, 2026

The Sherman Theater is Stroudsburg’s nonprofit, 1929-era hub for concerts, theater, and community events, with a full bar and concessions that keep the nights easy. When you want something up-close, slide next door to the Sherman Showcase for local bands, comics, and emerging talent.

From the East Stroudsburg newsletter, October 24, 2026