4 Great Small Town, Fall Towns

Fall in the Pennsylvania Pocono Mountains

There’s something about a vacation in fall that is just a bit extra – the crowds are gone, it’s OK to spend some time inside since your summer tan has come and probably gone and the fall colors are an attraction in themselves. Add a bit more to the magic by enjoying some small-town charm when glamping this fall.

Cabin at Thousand Trails Wilderness Lakes
Cabin at Thousand Trails Wilderness Lakes

Temecula, California: Pick a glamping cabin or cottage at Thousand Trails Wilderness Lakes in Menifee and you’re less than 20 miles from Temecula – a tiny town with a chill vibe that has been named one of the most charming small towns in Southern California. Temecula is located in California’s South Coast Wine Region and there are more than 40 wineries here. Check out Briar Rose Winery, where the buildings are replicas of Snow White’s cottage or Longshadow Ranch Vineyards and Winery with a true old west feeling and cozy bonfires every Saturday night through November 18. Old Town Temecula is a perfect mix of old and new with antique stores, boutiques, craft breweries, and plenty of places to enjoy a bite to eat.

California’s Yosemite Area: While this part of California is best known for the magnificent National Park found here – we’re talking about Yosemite National Park – there are also several charming small towns that can serve as side trips when visiting here. First things first, book one of the fantastic glamping accommodations at Thousand Trails Yosemite Lakes, which include yurts and cabins. Once you’re settled in, take in the beauty of your location during autumn and the charm of the surrounding towns. Sonora, a historic Gold Rush town, is home to the Indigeny Reserve which has the perfect fall offerings of hard apple cider and apple brandy tastings. For a beautiful fall hike, check out the Dragoon Gulch Trail, a 1.2-mile (moderate) loop. Jamestown, another Gold Rush town, is also worth a visit. Railtown 1897 State Historic Park is good for a look at historic steam trains as well as some Hollywood history. And, the town has several wine tasting rooms as well as a craft brewery. You can also pan for gold, shop, and stroll the Walk of Fame to see which Jamestown locations have been featured in movies and television.

Cabins at Thousand Trails Timothy Lake South
Cabins at Thousand Trails Timothy Lake South

Milford, Pennsylvania: The perfect mountain town to visit during fall, Milford is located in Pennsylvania’s Pocono Mountains. Plan a glamping stay in a comfy cottage at Thousand Trails Timothy Lake South and take in this picturesque small town. The Black Bear Film Festival is set for October 13-15 and includes a weekend full of indies and short films. Want to see Pennsylvania’s tallest waterfall? That would be Raymondskill Falls, found in the Delaware Water Gap National Recreation Area, which is also a great spot for biking and hiking, plus some pretty great leaf-peeping. For some interesting history, visit Grey Towers National Historic Site, which was the home of Gifford Pinchot, the first Chief of the US Forest Service. Visitors can tour the mansion and the grounds of this estate that was completed in 1886. Milford also offers plenty of shopping and dining opportunities.

Cottage at Greys Point Camp in Topping, VA
Greys Point Camp in Topping, VA

Virginia’s River Realm: Dotted with charming small towns, Virginia’s River Realm is the area where the Rappahannock River meets the Chesapeake Bay. It is all about the simpler life and a trip here in fall promises to be a pleasant glamping getaway. Book a cottage stay at Grey’s Point Camp in Topping and let the fun begin. The Holly Point Art & Seafood Festival is set for October 15 in Deltaville and offers seafood, live music and unique artwork from 60 different vendors and the always-popular annual Urbanna Oyster Festival is scheduled for November 3 and promises all things oyster! Shopping in Kilmarnock is an option with several boutiques and antique stores while Deltaville has a maritime museum and the beautiful Holly Point Nature Park with walking trails and kayaking opportunities. Several towns have regular farmer’s markets, and they include Irvington, Kilmarnock, and Deltaville while Urbanna has a spectacular seafood market. To learn more about the River Realm and its charming towns, check out virginiasriverrealm.com.

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