On a short trip, there’s something wonderful about parking your car and walking everywhere you want to go—shops, restaurants, bars, craft beverage tasting rooms, theaters, and more. It makes for a relaxing getaway. You can experience that type of relaxation in Stroudsburg, Pennsylvania, about a two-hour drive north of Philadelphia and 15 minutes from the Delaware Water Gap. The historic 1.8-square-mile city has a thriving downtown with plenty to do crammed into just a few blocks.
In 1779, Colonel Jacob Stroud founded Stroudsburg on land that the Lenni Lenape inhabited before European settlers came to the region. Stroud Mansion, built for one of Jacob’s sons, still sits on Main Street and is now the home of the Monroe County Historical Society Museum. There are beautiful houses to stroll by in the city’s historical district, but food and drink lovers have many other reasons to visit Stroudsburg.
Those who want to take in the culinary scene of the city can eat and drink their way up and down Main Street during a getaway and still not experience everything the city has to offer. It might take more than one trip to take in all Stroudsburg has to offer, particularly if you want to also attend one of the summer’s many concerts or festivals, which take place on Main Street or at Courthouse Square, just a block away.
9 am
HIT THE FARMERS MARKET
If you’re spending Saturday in Stroudsburg and you get there early in the day, your first stop must be the year-round Monroe Farmers Market at Courthouse Square. The market’s summer hours are 8am to noon. Support local producers by buying produce, cheese, honey, chocolate, eggs, and more. (Think about bringing a cooler with ice packs to leave in the car, and drop your purchases off while you enjoy the rest of your day.)
10 am
ENJOY BREAKFAST
The welcoming 7th Street Coffee has comfortable indoor, front sidewalk, and back patio seating. The menu is full of coffeehouse classics: cappuccino, espresso, coffee, tea, and cold brew as well as tasty breakfast sandwiches and pastry choices. A posted Wi-Fi password gives you permission to open your laptop and check your email, if you must.
11 am
SUPPORT THE SECONDHAND ECONOMY
If you want a break from nonstop eating and drinking, take some time to browse pre-loved books, music, and clothing. Find a treasured volume at Carroll & Carroll Booksellers with its shelves and floor piles of used and rare books. Hunt for music at Main Street Jukebox with its bins of vinyl, CDs, and cassettes, plus music-themed books and collectibles. Finally, shop curated women’s resale in the very organized DeNovo Clothing Exchange.
12:30 pm
GRAB IRISH FARE FOR LUNCH
Siamsa Irish Pub, one of a handful of Irish establishments on Main Street, is located in an old bank. Enjoy a pint, a cocktail, or glass of wine at the bar or one of the many tables. Seriously consider the fish and chips, served hot and crisp. There’s an entire menu of Irish standards and traditional pub food, so it can be tough to choose.
2 pm
EXPLORE THE CRAFT BEVERAGE SCENE
If you’re in the mood for a drink, you’ll have no shortage of options. Within just two blocks, you’ll find seven tasting rooms offering local wine, beer, and mead—each with its own vibe.
Wine lovers might gravitate toward the intimate RAW Urban Winery, where you can sample a flight of five wines, or the larger, livelier Renegade Winery, which often features live music and allows you to have tacos from nearby E’Z Taqueria delivered to your table. Tolino Vineyards’ tasting room offers a warm, friendly atmosphere where regulars are greeted by name.
Prefer beer or cider? Head to Main Street, where three breweries offer different experiences. Bovinos pours its own brews and ciders (the slightly sweet Rosie’s Red cider is a standout) alongside a full menu of pub fare. Down River Brewing Co. pairs its pours with a classic pub menu and axe throwing, while Signature Brewery and Saloon leans into a country-western theme with line dancing, music bingo, and more.
At the Nordic-inspired Stonehaüs Meadery you can try one of a dozen meads crafted from fermented honey.
With so many choices so close together, you can pick one or two that match your mood—and maybe bookmark a few more for your next visit.
6 pm
TIME FOR DINNER
If you’re up for finer dining, Garlic Restaurant and Bar has a menu of modern American classics. Share the perfectly prepared Black Jack small plate—filet medallions with a bleu cheese sauce and garlic bread—before diving into your main dish. Or visit the casual La Morena BBQ, a BYO that serves barbecue and Portuguese cuisine, where the empanadas are a customer favorite.
8 pm
ENTERTAINMENT TIME
The Sherman Theater, with its historic, restored original architecture from 1929, hosts live concerts—both original and tribute acts—stand-up comedy, festivals, and more. If you’d rather not sit still for your entertainment, Mayhem Amusements Arcade lets you revisit your days of playing coin-operated pinball and retro games like Galaga with other adults also reliving their youth.
Stay the Night
You can head home at the end of the day or stay at the historic, recently renovated Penn Stroud Hotel right on Main Street. It’s just steps away from all there is to do. Guests get free parking in the onsite parking lot and free breakfast in the morning.
Before heading out of Stroudsburg, consider stopping just a few miles away in East Stroudsburg, a university city with several good restaurants clustered together on Crystal Street. Enjoy brunch and a flight of mimosas at Farmhouse, where the food is made from scratch. Lunch can be found at Trackside Grill & Bar, known for its burgers, wings with specialty sauces, and sushi. Or if you simply want a sweet treat before your drive home, gelato or an ice cream sundae from Jimmy’s Ice Cream is a decadent way to end your Stroudsburg region adventures.
EDITOR’S NOTE
Edible Lehigh Valley covers this area all year round. Pick up a copy while you’re visiting to learn about even more fun things to do.
Summer 2025
COMMUNITY EVENTS
Downtown Stroudsburg comes alive in the warmer months with festivals, art walks, live outdoor music, and artisan markets. These community events bring out locals and visitors alike.
FIRST SATURDAY ART WALK: From April through October, on the first Saturday of each month, all the downtown galleries open their doors to display new works and feature artists. 6pm to 8pm.
CONCERTS IN THE SQUARE: On Thursdays, from June 6 through August 21, local musicians play at Courthouse Square while kids are entertained by family-friendly activities. 6pm to 8pm.
STROUD FEST: On August 31, the downtown turns into a large festival with a vendors’ row on Main Street, multiple stages for live music, and a food court at Courthouse Square. 11am to 6pm.
ARTISANS ON ANN: On August 30, 70+ artisans and vendors gather on Ann Street in American Ribbon’s parking lot. The event coincides with Stroud Fest. 9am to 4pm.
IRISH AMERICAN FESTIVAL: On September 6 at Courthouse Square, celebrate Irish American Heritage with music, food, drink, dance, and fun. 11:30am to 8pm.
Stroudsburg
7TH STREET COFFEE
20 N. 7th Street
570.213.9973
7thstreetcoffee.net
BOVINO’S BREWERY
610 Main Street
570.269.1029
bovinos-brewery.com
CARROLL & CARROLL BOOKSELLERS
740 Main Street
570.420.1516
DENOVO CLOTHING EXCHANGE
586 Main Street
570.424.1132
facebook.com/DeNovoClothingExchange
DOWN RIVER BREWING COMPANY
569 Quaker Alley
570.213.5110
downriverbrewing.com
E’Z TAQUERIA
572 Main Street
570.664.9932
eztaqueria.com
GARLIC RESTAURANT AND BAR
907 Main Street
570.350.6868
garlicrestaurantbar.com
LA MORENA BBQ
620 Main Street
570.422.1110
facebook.com/LaMorenaBBQ
MAIN STREET JUKEBOX
606 Main Street
570.424.2246
mainstreetjukebox.com
MAYHEM AMUSEMENTS ARCADE
619 Main Street
570.212.9226
www.mayhemamusements.com
MONROE FARMERS MARKET
The Courthouse Square, 38 N.
7th Street
monroefarmersmarket.com
THE PENN STROUD
700 Main Street
570.421.2200
thepennstroud.com
SIAMSA IRISH PUB
636 Main Street
570.421.8434
siamsairishpub.com
SHERMAN THEATER
524 Main Street
570.420.2808
shermantheater.com
STONEHAÜS MEADERY
429 Main Street
570.234.3600
stonehausmeadery.com
RAW URBAN WINERY
616 Main Street
570.350.2697
rawwinery.com
RENEGADE WINERY
600 Main Street
570.350.2638
therenegadewinery.com
SIGNATURE BREWERY & SALOON
564 Main Street
570.213.5110
signaturesaloon.com
TOLINO VINEYARDS
39 N. 7th Street
272.200.2990
tolinovineyards.com
East Stroudsburg
FARMHOUSE CRYSTAL
15 Crystal Street
570.420.7522
farmhousepoconos.com
JIMMY’S ICE CREAM
75 Crystal Street
570.664.8685
facebook.com/JimmysIceCream18360
TRACKSIDE GRILL & BAR
50 E. Crystal Street
570.424.3200
tracksidestationgrill.com
