How to spend a scenic fall weekend in Delaware Water Gap, Pa. | Field Trip

We Philadelphians tend to have a very specific (urban) reference point for the Delaware River: water churning behind the ferry as it chugs to a concert in Camden, ripples snapping at the edges of Penn Treaty Park, or the pilings of Morgan’s Pier.

So visiting Delaware Water Gap, a majestic 40-mile stretch that winds through the Appalachians, can feel like seeing the river you’ve known all your life for the very first time.

Delaware Water Gap is also the name of the affable, outdoorsy village that serves as a launching point for river trips and Appalachian Trail hikes. Paired with the nearby Poconos university towns of Stroudsburg and East Stroudsburg — and plenty of fall foliage — this getaway two hours north of the city makes for a scenic, slow-paced weekend.

Ten rooms with antique chairs, original hardwood, and en suite bathrooms fill the Deer Head Inn, a historic double-balconied inn in the center of Delaware Water Gap.

It’s also a nationally renowned music venue, with its own record label and a lounge that’s hosted decades of jazz greats, including pianist John Coates Jr. After a day outdoors, nothing beats a nightcap with live music.

📍 5 Main St., Delaware Water Gap, Pa. 18327

Kayak, canoe, paddleboard, boat — there are many ways to enjoy this scenic stretch of the Delaware. In early fall, trade the summer tubing for a gentle paddle, as the trees along the river flare gold and crimson. Edge of the Woods Outfitters, right in town, supplies the gear and maps for self-guided two- to four-hour adventures that glide through light rapids and still pools.

📍 129 Main St., Delaware Water Gap, Pa. 18327

The wooden sign of a hot dog and apple pie slice holding hands (the “True Love” special, $4.95) is just a preview of what’s inside Village Farmer and Bakery. This beloved, family-run bakery offers: breakfast sandwiches on French toast, pierogies, fruit preserves, cannoli, lobster rolls, chocolates, and saucer-sized cookies. Apple pies (double-crusted or crumb, with or without walnuts) may have built this house, but there are nearly 30 other varieties, including red raspberry, coconut custard, and shoo-fly.

📍 13 Broad St., Delaware Water Gap, Pa. 18327

Join the vintage hounds at this 22,000-square-foot antiques warehouse just off Stroudsburg’s main street. With more than 100 independent vendors, Olde Engine Works is part treasure hunt, part time machine. Federal-style desks, carved ducks, Whitney Houston vinyl, possibly haunted dolls — it’s all here. Bring patience and layers; the old warehouse gets chilly as the weather cools.

📍 62 N. 3rd St., Stroudsburg, Pa. 18360

Fans of historic indie theaters will love this adorable four-screener, which dates all the way back to 1884 in downtown East Stroudsburg. Pocono Cinema and Cultural Arts Center is the perfect rainy-day (or chilly-night) stop for an art-house flick or blockbuster. Order popcorn and settle in under the glow of the marquee.

📍 88 S. Courtland St., East Stroudsburg, Pa. 18301

A sake distillery … in the Poconos? Believe it. This friendly spot on Delaware Water Gap’s main drag crafts several different styles, including a dry-hopped sake whose floral nose and crisp bitterness cut through chilly mountain air. Sango Kura’s full kitchen turns out cozy Japanese hits like karaage chicken and tonkatsu ramen, perfect after a day on the trail.

📍 39 Broad St., Delaware Water Gap, Pa. 18327

From Japan to Peru, end the day at Llama Ice Cream, a cottage creamery just beyond the riverbanks in East Stroudsburg. They make the classics, but the best flavors nod to owner Julio Amenero’s native South America — tangy soursop, creamy mamey, and rich dulce de leche. A scoop pairs perfectly with a crisp fall evening walk along the river.

📍 266 River Rd., East Stroudsburg, Pa. 18301