Thousands of miles of trails span the U.S., and these charming small-town hikes should be noticed. In traveling, I seek out off-the-beaten-path places that captivate me with their story, and these five towns are a breath of fresh air. Wander into these destinations unknown and discover the allure of the outdoors and the hometown places to stay for something unique and fulfilling this summer.
MILFORD, PA
Meet the little-known Pennsylvania Town known as the birthplace of the American Conservation Movement—the town where the U.S. Forest Service was born offers some incredible outdoor experiences. The hike to explore- Cliff Park to Raymondskill Falls Loop, provides an up-close view of Pennsylvania’s tallest waterfall, Raymondskill Falls.
This loop hike offers dramatic views along the winding Delaware River cliff, Kittatinny Mountain, and even High Point in New Jersey. This gateway to the Poconos is less than two hours from New York City and is complete with great restaurants and watering holes. Not to mention, Lake Wallenpaupack is nearby.
Where to Stay
A storied, picturesque boutique hotel on Broad Street is home to dining, event space, and a speakeasy and is known as a great base camp for outdoor adventure. Pro-tip: Sit at the very cool bar and try one of the Italian-inspired Martinis.
If walls could talk… This luxury boutique hotel has hosted some high-ranking leaders- think John F. Kennedy, Theodore Roosevelt, and Bob Marshall. It is now home to fine food, luxury accommodation, and tribute photos to Andy Warhol. Pro-tip: indulge at Bar Louis, an unexpected vibe in this small town.
WESTBROOK, CT
Named the 2023 best state in America for hiking by Thrillist (I know, I said Connecticut for hiking! But it is true and an incredible state to see the forest), Connecticut offers gorgeous outdoor exploration. Explore Gillette Castle State Park for a truly unique experience.
Hike to a medieval stone castle perched above the Connecticut River, built in 1914 by William Hooker Gillette, the actor, director, and playwright most famous for his portrayal of Sherlock Holmes. With 184 acres of woodlands, this outdoor wonderland offers views of the river (watch the Riverboat cruise along) and sits atop the most southerly hill in a chain known as the Seven Sisters.
Where to Stay
This charming New England Inn is known for its hospitality, Sleep Number beds for incredible rest (literally the best sleep I have had at a hotel), and the most convenient location to explore all this area of Connecticut shoreline offers. It is located within two hours of New York City and Boston. Pro-tip: Sit outdoors by the firepit overlooking the river during the summer.
WIMBERLEY, TX
Wimberley is an outdoor mecca with vibrant Texas vibes named DarkSky Place of the Year by DarkSky International (November 2023). 2024 has been dubbed the year of astro tourism, and this designation is bringing more people to the humble town in the Texas Hill Country.
For shorter, easier hikes, visit Jacob’s Well, where you can cool off in the water (except during drought years, but still worth seeing). Enjoy the 0.2-mile out-and-back Old Baldy Trail for a grand view of Wimberley. Wimberley offers several great watering holes and food options and is minutes from great, picturesque wineries and breweries.
Where to Stay
A quiet luxury 25-acre ranch with 360-degree sunset views. The perfect place to get away from it all and view the stars at night or enjoy an outdoor movie under the vast sky. Pro-tip: Be at the Ranch for sunset, some of the best I have experienced.
SWAN VALLEY, ID
While known as a fly-fishing paradise to anglers across the globe, Swan Valley, Idaho, offers some gorgeous off-the-beaten-path hiking and is home to Southeast Idaho’s most scenic landscape.
The small town is a rugged mountain paradise. Hike Palisades Creek Trail to Lowers Palisades Lake for an unforgettable experience. Spot for deer, elk, cougar, mountain goats, and black bears. The trail runs alongside the creek with several bridge crossings and a nice steady climb. You will be mesmerized at every step.
Where to stay
This mountain lodge offers six large suites (lots of room!) that can accommodate multiple people. It is the perfect adventure spot to stay, with a restaurant and daily complimentary breakfast. Relax, play pool, or sit outside in the fresh, open air. Fishing packages are also available. Pro tip: order a picnic lunch to go (you can call and pre-order even if you are not a guest).
ALLEGAN, MI
Surreal hiking along the Kalamazoo River at Armintrout-Milbocker Nature Preserve, SWMLC, is a breath of fresh air. This preserve is richly intertwined with The Kalamazoo River and the identity of downtown Allegan.
There are 80 upland acres of pine-oak forest, 60 acres of wetlands, and over 560 documented plant species — demonstrating the land’s biodiversity and the importance of protecting it. This land is stunning and unexpected in the historic town of Allegan.
Where to stay
This historic home, converted to a luxurious bed and breakfast, provides an elegant stay complete with a gourmet breakfast. Victorian design and modern style offer experience and charm in this quaint country town. Pro-tip: Enjoy time relaxing on the home’s amazing porch, and make reservations for dinner at Salt of the Earth.
Spending time in nature is always good for my soul, and I hope you will fall in love with these off-the-beaten charming destinations as much as I have.
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