Historic Small Town Walks: Self-Guided Summertime Tours in 5 Poconos Villages

Milford: Conservation & Gilded-Age Charm

Historic Walk Milford

Start your Milford journey at the Columns Museum, home of the Pike County Historical Society. Pay a visit to the exhibits to learn about local history and see the Lincoln Flag, which cushioned President Abraham Lincoln on the tragic night of his assassination in 1865. Head deeper into town along Broad Street and stroll past the imposing Pike County Courthouse and charming 19th century boarding houses like the Tom Quick Inn, an 1800s stage coach stop now home to the Varsity Room Speakeasy, and the Hotel Fauchere, founded by a Swiss hotelier who once served as Master Chef at New York’s Delmonico’s.

Small Town Shops and Stops

At the same intersection where Hotel Fauchere stands, you'll find Betterworld Store & Cafe, the perfect stop for morning coffee, and Jive Bar & Lounge, the perfect stop for evening drinks. Venture a few blocks down Catherine Street to discover Health House, which offers the latest wellness treatments, and the historic Milford Theater & Performing Arts Center, which has a fantastic lineup of concerts, movies, and more.

The Pinchot Legacy

Backtrack to Broad and follow the street until it reaches Route 6, called Harford Street as it passes through Milford, where you'll find the Historic Forest Hall. Once home to the Yale Forestry School's summer program, this beautiful building is one of the marks the Pinchot family left on Milford. Gifford Pinchot was the first chief of the U.S. Forest Service and has been called the Father of the American Conservation Movement due to his commitment to protecting the country's natural resources. Right across from Forest Hall, the Pinchots' first home in town is now home to the Milford Community House, which hosts free concerts every Saturday through the summer. The Pinchots later built spectacular Grey Towers National Historic Site which, although a bit far for a walk, is well worth a visit!

Map Out Your Milford Walking Tour

Plan your route using the map points below. Click here to view a pictorial map of the downtown area and find more walking tours through the Pike Chamber. Find even more information on our Milford page and check out things to do in the area.

Honesdale: Rail History & Main Street Finds

Historic Walk Honesdale

Honesdale is known as the birthplace of the American Railroad, so it's no surprise the town's Main Street is stretched our parallel to the train tracks. Starting from the south side of town, you'll pass tasty restaurants like Native, Here & Now Brewing Company, and Camp Umpy's Bagels & Stuff, a great spot to grab breakfast before starting off on your walking tour. As you continue up the street, you'll find the visitors center in the train station where The Stourbridge Line excursions depart for scenic, seasonal trips along the Lackawaxen River. Just next door to the station is the Wayne County Historical Society & Museum, where you can see a recreation of the Stourbridge Lion, the first steam locomotive to run on US commercial tracks.

Stop in Central Park

Walk a block down 9th Street to see Honesdale's Central Park and the Wayne County Courthouse. Enjoy free concerts in the park on Monday and Thursday nights thanks to the Wayne County Creative Arts Council Summer Concert Series or sign up for one of the Old Stone Jail Open House tours. Keep an eye out for the Pennsylvania historical marker dedicated to Honesdale native Richard Smith, who wrote the classic holiday song Winter Wonderland, inspired by the beautiful Wayne County winters.

More on Main Street

Return to Main Street to drop in boutiques like Gather and Maude & Main or see what's going on at The Cooperage Project, a community hub that hosts a farmer's market as well as concerts and shows. Tucked away down Chapel Street, the Runaway Train Brewery is a great place to enjoy some drinks and snacks at the end of your walk!

Bird's-Eye View

Want an aerial view of the streets you've been walking? If you're up for an extra trek, turn right on Park Street and find the start of the Irving Cliff trail. You'll find a beautiful view waiting for you at the top!

Map Out Your Honesdale Walking Tour

Plan your route using the map points below. Find even more information on our Honesdale page and check out things to do in the area.

Stroudsburg: Murals, Markets & Music

Historic Walk Stroudsburg

Stroudsburg was founded by Revolutionary War Colonel Jacob Stroud, who built the Stroud Mansion as a home for his son. The mansion is now home to the Monroe County Historical Society which offers walking tours and a detailed guide to the historic buildings in town. Cross Main Street and head just a few blocks down 9th to visit American Ribbon Craft and Fabric, which was home to the Monroe Silk Mills for a hundred years and still offers a great selection of craft goods. Don't miss The Potting Shed, full of plants and gifts, right behind it!

Stroll and Shop down Main Street

Continue your walk down Main Street and keep an eye out for murals! They're dotted throughout town: there's a train coming out of the wall next to Just Like Magic Bakery, a parade of performers opposite the Sherman Theater, and so much more. As you pass The Penn Stroud Stroudsburg on the corner, turn left on 7th Street to check out the historic square in front of Monroe County Courthouse, which serves as a hub for seasonal events and the Monroe Farmers Market every Saturday. Browse the scents at Pocono Soap or peruse the canvases at the Andrei Art Gallery and Studio before you return to Main Street.

Night on the the Town

If you're planning to explore the Pocono Beverage Trail, there are plenty of walkable destinations to visit in Stroudsburg! Sip wine at the tasting bar at Tolino Vineyards, raise a glass at RAW Urban Winery and Hard Cidery, or head to Signature Brewery & Saloon to try line dancing. Get tickets to see a concert at the Sherman Theater, the perfect place to end your walking tour of Stroudsburg and a great spot to spend a night out.

Map Out Your Stroudsburg Walking Tour

Plan your route using the map points below. Find more walking tours through the Monroe County Historical Association. Find even more information on our Stroudsburg page and check out things to do in the area.

Hawley: Lake-Linked Heritage

Begin in Bingham Park

Located right alongside historic Route 6, the charming small town of Hawley is the perfect place for a pit stop or overnight stay! Stop at The Settlers Inn for the night or delicious fine dining. This arts and craft lodge is right across the street from Bingham Park, where you can launch a kayak, take a stroll, let the kids enjoy the playground, or catch summer events like Arts and Crafts Fair.

Discover Downtown Gems

As you cross the bridge over the Lackawaxen River to continue down Main Avenue, you'll pass Pennsylvania Rail Bike on your right and the Hawley Public Library on your left. Cross over Middle Creek to enter the downtown stretch, lined with picturesque storefronts and unique businesses like the Crazy Country Club. Turn down Keystone Street to watch great acts at the Ritz Company Playhouse or browse the wide variety of goods at The Grains Book Store and Gift Shop.

Historic Walk Hawley

Hawley has a beautiful Riverside Park and Trail that can be picked up just down River Street off Main. Click here to view the full trail guide! Walk along the high banks over the Lackawaxen then cut up Paupack Street and Falls Avenue to get a glimpse of Ledges Hotel perched next to beautiful Paupack Falls. Further up the hill, you'll find the historic Hawley Silk Mill, now home to galleries and shops including the Cocoon Coffeehouse & Bakery, located in the building that used to house the silkworms.

Hike to the Lake

Up for even more of a trek? Head back down to rejoin the Hawley River Walk below Ledges Hotel and cross the Cromwell Street bridge to pick up the Gorge Trail, part of the Lackawaxen River Trail system. This 1.6 mile rough terrain trail leads to the shores of Lake Wallenpaupack!

Map Out Your Hawley Walking Tour

Plan your route using the map points below. Click here to learn more about the Hawley Trail. Find even more information on our Hawley page and check out 50 things to do in the area.

Jim Thorpe: Victorian Streetscapes & River Views

Historic Walk Jim Thorpe

Start at the Jim Thorpe Visitors Center in the turreted train station, where the Lehigh Gorge Scenic Railway departs on trips alongside the Lehigh River. On the far side of the tracks to the south, the Mansion House Bridge leads to nature walks along the D&L Trail in Lehigh Gorge State Park, but for a downtown stroll, you'll want to cut through Josiah White Park in front of the train station and cross the street under the Carbon County Courthouse clock tower to get your first glimpse of Broadway.

Millionaire Mansions

The anthracite coal that ignited the American Industrial Revolution was mined in the hills of Carbon County, and the millionaires who made their fortunes from it built beautiful homes and buildings in town. Take a detour around Hazard Square up Packer Hill to see two of these opulent mansions, the Asa Packer Mansion, now home to a museum, and the Harry Packer Mansion Inn, now home to a bed and breakfast that hosts murder mystery weekends.

Climb the Hill to See the Old Jail

Return to Broadway and make your way up the winding street, past landmarks like the quaint Inn at Jim Thorpe and the beautiful brick Dimmick Memorial Library. The imposing Mauch Chunk Opera House stands where the road curves, with the Marion Hose Bar, located in the old firehouse, tucked just beside it. Make a stop in the Mauch Chunk Museum & Cultural Center to view exhibits on the history of Jim Thorpe then continue past the floral facade of Ma's Crepes & Cakes and you'll soon see the bulk of the Old Jail Museum looming above you. This jail was the site of the infamous Molly Maguires trial in the late 1800s. Take a tour to learn all about it!

Wander down Race Street

As you turn your steps back down the hill to return to the train station, don't miss the chance to explore Race Street. This aesthetic alleyway branches off from Broadway in front of Dolon House and leads to Historic Stone Row, where colorful doorways lead to chic shops and bed and breakfasts. Where Race Street rejoins Route 209, you'll find the stunning St, Mark and St, John Episcopal Church, which offers its own walking tours.

Map Out Your Jim Thorpe Walking Tour

Click here to view a detailed walking map of Jim Thorpe or plan your route using the map points below. Parking is available in the Carbon County Parking Lot, but keep in mind it can fill up quickly on weekends! Find more information on our Jim Thorpe page.

Pocono Small Town Walking Tours

These small towns are just the beginning! Explore our area and discover even more history in boroughs like Delaware Water Gap, Lehighton, and Lansford. Browse more driving and guided tours or sign up for our free Pocono Experience Passports to make the most of your time in our region!