Exploring Delaware Water Gap and Stroudsburg: Nature's Beauty and Small-Town Fun

My knowledge of Pennsylvania is vast, or at least I thought so. That is, until I stumbled upon some information while researching places where the fall foliage display is the most dramatic. It turns out that Delaware Water Gap, nestled in Monroe County near the Delaware River and known as the Eastern Gateway to the Poconos, takes the prize as one of the more-striking areas for viewing fiery fall foliage by foot, bike, kayak, or as in my case trolley. What surprised me the most, however, is that the small borough is also home to the oldest, continuously operating jazz club in the United States.

After touring Delaware Water Gap, I continued on to downtown Stroudsburg—a funky, friendly place where thrift shops co-exist with boutique shops and street art is intermingled with galleries. The walkable area attracts many a Delaware Water Gap visitor looking to shop, dine and perhaps take in a show.

The Trolley Tour

Pocono Day Trippers offers Trolley Tours in Delaware Gap

The easiest way to learn about Delaware Water Gap and its history is to sign up for a Pocono Historic Trolley Tour offered by the PoconoDay Tripper. When I visited, Pocono Joe regaled riders with tidbits about the area and how it was once the second most popular inland destination in the United States. On the tour, Joe also points out structures like the Castle Inn. 

The Castle Inn dates back to 1906.

Built in 1906, it once attracted many tourists seeking to escape the heat of the city and was the area’s first resort with running spring water and electricity. The tour also includes a drive through the Shawnee Inn Golf Resort, which was established in the late 1890s when a native New Yorker and business owner Charles Campbell Worthington made it his summer home. Over the years, the Golf Resort has hosted celebrities like Jackie Gleason and Arnold Palmer.

Riders will also hear how Fred Waring made his mark on the area. 

Fred Waring was a Penn State grad, a band leader and an entrepreneur.

Those of a certain age may have heard of Fred Waring and the Pennsylvanians, mostly due to Christmas albums that played in households once a year. Waring, a Penn State grad, brought to market an invention which helped revolutionize the American kitchen: the Waring blender. According to Pocono Joe, Waring was fond of using it to mix drinks for his musician friends.

Trolley Riders will also be able to disembark to take photos of scenic Buttermilk Falls, which flows down a series of rocky ledges and is a favorite spot for photographers, especially as the trees explode in a riot of color during the autumn season.

Buttermilk Falls is a scenic trolley stop.

We also stopped at a small church, which housed the Slate Belt Historical Museum and listened to an old Victrola. Now I understand why the old movies sound so "tinny."

We also saw this impressive carousel lion carved by a man named Charles Loof, who opened a carousel factory in 1880. After Loof died, this lion ended up, aptly, in a local Lions Club. You can read the story of this impressively carved lion below.

The story of the carousel lion at the Slate Belt Historical Museum.

Another stop on the trolley tour was a trip to a small town called Portland, where we picked up some chocolates at the Alexandra and Nicolay chocolate shop, and the Shawnee Inn and Golf Resort, which dates back to 1911.

The Shawnee Inn dates back to 1911.

The Shawnee Playhouse

The trolley also passed by the Minisink Inn, built in the 1740s on land purchased from American Indians. It has served as a stagecoach stop, general store, hotel and now a tavern.

The Minisink Inn.

The trolley trip takes between 1.5 and two hours and requires pre-registration on the Pocono Day Tripper website.

Peter Luck, owner, said, “It’s so rewarding when people tell me they enjoy the tour and our local history. It means everything to me.”

All That Jazz

The porch at the Deer Head Inn.

The Deer Head Inn is a Victorian style building with two stories of sprawling wrap-around porches, perfect for relaxing during warmer months as the music wafts its way outside. Built between 1853 and 1865, it was originally called the Central House and was renamed The Deer Head Inn in the 1930s.

The bar at the Deer Head Inn.

Jazz enthusiasts have been known to flock to the destination, especially for the annual Jazz Fest that is held the weekend after Labor Day. Those who are interested in staying awhile can choose from among eight rooms and two suites.

The stage at the Deer Head Inn.

Ian Carrig, nephew of owner Dennis Carrig, lists some of the jazz artists who have played at the club, including Stan Getz, Keith Jarrett, Phil Woods, Urbie Green, Nellie McKay and Nicole Glover, to name a few. Carrig works as chef at the establishment and turns out dishes like crab cakes, baked salmon, shrimp scampi, burgers, sandwiches and more.

Funky, Fun and Friendly Downtown Stroudsburg

Public art in downtown Stroudsburg.

Restaurants and small, independent shops are plentiful downtown.

If you like getting your shop on, look no further than downtown Stroudsburg, where you’ll find clothing boutiques, thrift shops and galleries tucked among eateries, bars and street art.

Grandpa Joe’s offers friendly service at their candy shop located at 730 Main Street. There you can find a wide range of candy, both modern and retro. 

Black Cow, Slo-Poke, Zagnut and Zotz are just a few of the candies available at Grandpa Joe's.

When I visited, they were handing out popcorn-flavored taffy and enjoying people’s reactions. (It was surprisingly good.) Not far from Grandpa’s is Carroll & Carroll Booksellers, an independent book store dating back to 1991 and selling new, used and rare books. 

And for antique lovers, there’s Olde Engine Works. Located at 62 N. Third Street, it’s one of the largest antique co-ops in northeast Pennsylvania.

If you work up a thirst while shopping, you may be interested to know that Stroudsburg is also home to Bovino’s Brewery, Stonehaus Meadery and the Raw Urban Winery and Hard Cidery, all on Main. Just outside downtown there’s the Mountain View Vineyard on Walters Road and the Eagles Rest Cellars at 188 Eagles Rest Lane. And for something a little different, there’s Sango Kura, Pennsylvania’s first and only sake brewery—but you’ll have to return to Delaware Water Gap to indulge in those libations.

You may also want to check out the historic Sherman Theatre, also located on Main. The theater dates back to early 1929 and today features comedians like Vic Dibitetto, (whom you may recognize as the man who does the “milk and eggs during a snowstorm” bit), musicians like Ace Frehley of KISS and various tribute bands, to name just a few of the acts that have entertained crowds just this year.

The Sherman Theatre dates back to 1929.

Whether you embark on a day trip, or stay a day or two, these suggestions should keep you busy as you explore eastern Monroe County—an area which offers a diverse array of experiences to cater to a wide range of tastes.