4 Great Small Town, Fall Towns

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.

Read More:

5 Things to Do In… Virginia’s Chesapeake Bay Area

Maymont Gardens in Richmond, VA

There’s a reason Virginia tourism still uses “Virginia is For Lovers” to entice visitors to the state. The slogan, which was first introduced in 1969, remains true today. What’s not to love about Virginia? It’s full of history, has produced more US presidents than any other state (eight, in fact), is known for its oysters, and other culinary delights such as blue crabs and Virginia ham, and offers all kinds of outdoor adventures from hiking to water sports. And one spot you will absolutely love is the Chesapeake Bay area.

Cottage at Bethpage Camp-Resort in Urbanna, VA

The Chesapeake Bay is an estuary between Maryland and Virginia. And the point where the Bay meets the Rappahannock River is known as the Virginia River Realm, a magical mix of shoreline, charming towns and one-of-a-kind experiences. Lucky for you, we have three great locations where you can settle in while exploring here. Bethpage Camp-Resort, in Urbanna, Greys Point Camp in Topping, and Chesapeake Bay RV Campground in Gloucester. Each of these locations has a number of cottages and cabins for you to make your home base while you explore the area. The towns of Topping and Urbanna are part of the River Realm and Gloucester is a charming town with roots dating back to Colonial Virginia.

Here are five ways to get to know the area:

  1. Day Trip to Richmond: About an hour west is Virginia’s capital city of Richmond, which offers a little bit of fun for everyone. Lewis Ginter Botanical Garden is 50 acres of amazing outdoor gardens (opens to the public July 16). Themed gardens include a Children’s Garden, Cherry Tree Walk, and the Rose Garden. The Virginia Museum of Fine Arts offers free admission and exhibits from around the world. Another option for an outdoor experience is Maymont, a Victorian estate with public parklands. While some of the exhibits are currently closed, the 100-acre estate offers plenty of outdoor parkland and gardens to explore. 
Lewis Ginter Botanical Garden. Richmond, VA
  1. Belle Isle State Park: Open from dawn to dusk, Belle Isle offers all kinds of outdoor activity from bird and wildlife viewing to hiking, biking, kayaking, and canoeing. The great thing is they offer rentals for canoes, kayaks, and bikes so you can travel lightly there and back.
  1. Virginia Oyster Trail: You absolutely cannot visit this part of Virginia without getting up close and personal with the bivalve that Virginia is famous for! The Virginia Oyster Trail (virginiaoystertrail.com) is a mix of oyster-focused sites that provides insight to the world of Virginia oysters.
Cottages at Greys Point Camp in Topping, VA
  1. Presidential Birthplaces: George Washington was born in Westmoreland County, Virginia, in 1732. The George Washington Birthplace National Monument is a national park where visitors can see a replica of Washington’s childhood home as well as a living colonial farm with historians to explain life as it was during Washington’s childhood. The James Monroe Birthplace Park and Museum honors our fifth president, James Monroe, who was born in Westmoreland County on April 28, 1758. Visitors can see the area where Monroe lived from birth until he left for college (College of William and Mary). A replica of the home is currently under construction, but the Visitors Center is open on Saturdays and Sundays and offers some history and artifacts.
Cabins at Chesapeake Bay RV Campground Gloucester, VA
  1. Deltaville: Known as the “Boating Capital of the Chesapeake Bay”, Deltaville is a delightful coastal town with shops, a maritime museum, and great places to eat crab cakes and oysters along the water. Consider booking a day sail, sunset cruise, or a fishing charter out of Deltaville.