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America’s Trails

Nine Romantic Trail Destinations That Will Make You Swoon

By: Amy Kapp, Laura Stark
February 10, 2020

View from the Ivanhoe Trestle along New River Trail State Park | Courtesy Virginia DCR
View from the Ivanhoe Trestle along New River Trail State Park | Courtesy Virginia DCR

With Valentine’s Day just around the corner, we thought it was a great time to bust out this list of top romantic trails in the United States, chosen for their “swoon-worthy” romantic views, date-worthy amenities and just plain good old-fashioned charm.

(And with Celebrate Trails Day just around the corner—you can never have too many great ideas in your rail-trail recreation arsenal!)

So without further ado, here are nine, great, romantic trail destinations to try and catch cupid’s arrow!

1. New River Trail State Park (Virginia)

New River Trail State Park | Courtesy Virginia DCR
New River Trail State Park | Courtesy Virginia DCR

With “Virginia is for Lovers” as the state slogan, it’s only fitting that a Virginia rail-trail kicks off our list, specifically the New River Trail State Park in the southern part of the state. This beautiful and relaxing 57.7-mile rail-trail has all the ingredients for a great date getaway, including scenic vistas, picnic spots, canoeing and kayaking, and even guided horse rides.

The mostly downhill (and pleasant) ride (from south to north) follows the Chestnut Creek and the New River and features several beautiful trestles, including the Fries Junction trestle bridge in the south, and the 950-foot Hiawassee trestle in the north (around mile marker 8).

2. Ke Ala Hele Makalae (Hawaii)

Ke Ala Hele Makalae follows the eastern coastline of the island of Kauai | Photo by Kevin Clark
Ke Ala Hele Makalae follows the eastern coastline of the island of Kauai | Photo by Kevin Clark

A key factor in choosing a destination for weddings? Weather of course. And that’s a big reason that Hawaii clocks in as the host of the second-largest number of destination weddings in America annually (topped only by—yep, you got it, Las Vegas)! Adding to the state’s romantic reputation is Ke Ala Hele Makalae, or “The Path That Goes by the Coast,” a breathtaking 17-mile developing multiuse trail that will eventually connect Nawiliwili to Anahola on the island of Kauai (known as the “Garden Isle”).

And of course it’s got everything you’d want in a warm-climate oasis: parks, beaches and the pinnacle Lydgate Park, which houses two lagoons for swimming, snorkeling and camping in relaxed ocean waters.

3. Napa Valley Vine Trail (California)

Napa Valley Vine Trail | Photo by TrailLink user tommyonbike
Napa Valley Vine Trail | Photo by TrailLink user tommyonbike

It probably doesn’t get much more romantic than California wine country—and now one can experience it via rail-trail on the developing 47.5-mile Napa Valley Vine Trail stretching from Vallejo to Calistoga, and featuring vineyards, green space and a staggering mountain backdrop. Trail users might check out the completed northern segment between Yountville to Napa, which features a number of parks—and offers connections to the in-progress 550-mile Bay Area Ridge Trail (Yountville), and the 500-mile developing San Francisco Bay Trail in Napa. All three trails help make up a larger 2,700-mile trail network being developed by the Bay Area Trails Collaborative, an RTC TrailNation™ project that will one day connect the entire Bay Area. 

Don’t Miss: Napa Valley Vine Trail Brings a Wealth of Benefits to California’s Wine Country

4. Cape Cod Rail Trail (Massachusetts)

Cape Cod Rail Trail | Photo by Stephen Struble
Cape Cod Rail Trail | Photo by Stephen Struble

Quaint New England towns, ocean views, sandy beaches—sounds like the Cape Cod Rail Trail in Massachusetts just might be the perfect recipe for a romantic getaway. The paved rail-trail travels for 22 miles through the southeastern peninsula and into Cape Cod National Seashore, connecting a half-dozen charming towns along the way.

In the north, Cape Cod seashore and its famous lighthouses; in the middle, Nickerson State Park with hiking, mountain biking, horseback riding and more; and in the south, Wellfleet, famous for oysters and featuring artisan shops and galleries.

Don’t Miss: Massachusetts’ Cape Cod Rail Trail | July 2017 Trail of the Month

5. Pine Creek Rail Trail (Pennsylvania)

Pine Creek Rail Trail | Courtesy Pine Creek Outfitters, Inc.
Pine Creek Rail Trail | Courtesy Pine Creek Outfitters, Inc.

For all you outdoor lovers out there, the Pine Creek Rail Trail oozes beauty and charm. The 62-mile well-maintained pathway makes its way through the bottom of Pine Creek Gorge, commonly known as the “Grand Canyon” of Pennsylvania for its überscenic saturation. (But don’t take our word for it! Check out the photo gallery on TrailLink.com.) Wildflowers, wildlife, lots of camping and lodging options, horse-drawn wagon rides and date-worthy restaurants in towns along the route help round out this magical affair with nature.

Don’t Miss: Pennsylvania’s Pine Creek Rail Trail | Sept. 2016 Trail of the Month

6. Ohio & Erie Canal Towpath Trail (Ohio)

Ohio & Erie Canal Towpath Trail | Photo by Bruce S. Ford, courtesy Summit Metro Parks
Ohio & Erie Canal Towpath Trail | Photo by Bruce S. Ford, courtesy Summit Metro Parks

We say “Ooh la la” for the Ohio & Erie Canal Towpath Trail, which features some of the best sights and experiences the Buckeye State has to offer. This includes the Cuyahoga Valley Scenic Railroad, a historical tourist railway that offers a variety of fun rides, including “Dinner on the Trail,” a two-hour, four-course dining excursion through Cuyahoga Valley National Park. Pair it with a bike ride (perhaps tandem?) along the Towpath Trail, and a date along the trail can’t get much better.

The Towpath Trail has a date with destiny as part of the expansive Industrial Heartland Trails Coalition’s 1,500-mile-plus trail network developing in eastern Ohio, western Pennsylvania, northern West Virginia and the southwestern corner of New York. Fittingly, the coalition’s slogan is “I Heart Trails.”

Don’t Miss: Ohio’s Ohio & Erie Canalway Towpath Trail | June 2016 Trail of the Month

7 – 9. A Bridge to Your Heart (Iowa, Nebraska and New York)

High Trestle Trail | Photo by Milo Bateman
High Trestle Trail | Photo by Milo Bateman

Sometimes, it take just a moment to change our lives forever—and this includes marriage proposals, sometimes nerve-racking, sometimes awkward, but forever beautiful when we look back on them years later. And right up there with romantic spots to pop the question are bridges, which—with the right lighting and backdrops—can invoke magical moods perfect for proposals.

A few of our favorites include: New York’s Walkway Over the Hudson—the longest pedestrian bridge in the world at about 1.6 miles and a member of the Rail-Trail Hall of Fame; the stunning Bob Kerrey Bridge connecting Omaha, Nebraska, and Council Bluffs, Iowa (the first dedicated pedestrian bridge to connect two states and a host of the 3,700-mile Great American Rail-Trail™); and the famous High Trestle Trail in Iowa, which—lined with 43 cribbings that include LED lights that come on at night—creates a brilliantly beautiful blue backdrop. For the latter—just ask Tyler and Ali Sloan, bicyclists who got engaged on the trail in 2013!

Walkway Over the Hudson | Photo by Aaron Schmidt
Walkway Over the Hudson | Photo by Aaron Schmidt

Don’t Miss: New York’s Hudson Valley Trail Network | March 2016 Trail of the Month


Related: A Moment on the Trail, A Lifetime of Happiness


Amy Kapp | Photo courtesy Amy Kapp
Amy Kapp

Amy Kapp serves as Editorial Director and Editor-in-Chief of Rails to Trails magazine. Kapp frequently writes about the impact of, and vast historical and cultural connections made by, America's rail-trails, parks and public lands.

Laura Stark | Photo courtesy Laura Stark
Laura Stark

Laura Stark is the senior editor for Rails to Trails magazine, responsible for highlighting trails and the people working hard to support them across America.

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