Ten Date-Worthy Hikes for You & Your Sweetheart


Bond with Bae Over a Mutual Love for the Great Outdoors

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You’re the type that spends most of your free time outside in dusty boots and well-worn technical fabrics. So how come you have to put on toe-pinching shoes and sit through an over-priced meal at a crowded restaurant when you want to go on a date?

The answer, of course, is that you don’t. Next time you’re planning a romantic good time, whether it’s with your longtime sweetheart or someone you’re just getting to know, make it a hike.

Because really, what bond could be more true than one formed over a mutual love for the great outdoors? Or, alternatively, if your potential boo is repulsed by a little dirt and sunshine, isn’t that something you’re better off knowing from the beginning (and, let’s be honest, likely immediate end)?

To encourage you along this route, we’ve put together a list of 10 date-worthy hikes in some of our favorite cities.

What makes a hike date-worthy? Here are our criteria:

  • Within a city or easily accessible from a city
  • Short. Can be done in an hour or two.
  • Has something cool about it like a great view or an unexpected rocky outcropping, or an adorable creek bridge, or a feeling of magical seclusion even though you’re literally a 5 minute walk from a major urban thoroughfare… that kind of thing.

Know a perfect hike that didn’t make our list? Click here to share it with a whole bunch of your fellow trail enthusiasts on SCA’s Facebook page. You’ll be doing the planet a favor by helping people who care about the great outdoors form connections that could lead to lifelong love and even–you never know–the creation of additional people who will grow up to care about the great outdoors…

Boston – Bumpkin Island – Boston Harbor Islands National Recreation Area

Once home to an American Indian settlement and, later, colonial tenant farmers, Bumpkin Island is now part of the Boston Harbor Islands National Recreation Area. Accessible by ferry, its meandering walking trails will take you by fields of wildflowers, slate and shell beaches, several campgrounds, and the spooky ruins of a children’s hospital and a WWI naval facility. Head here for more info.

Spooky ruins on Bumpkin Island, a romantic hiking and camping destination in Boston Harbor Islands National Recreation Area.Spooky ruins on Bumpkin Island. 

Portland – Pittock Mansion Hike in Lower Macleay Park

This rolling path through a thickly-ferned, moss-carpeted forest passes by a picturesque waterfall before it climbs, climbs, climbs up to a historic hilltop mansion and a stunning view of Portland and Mt. Hood, all easily accessible and within city limits. At the midpoint, you could easily imagine yourself lost in the wilderness. By the end, you’re just a few steps away from a quiet residential neighborhood.

Hiking date in progress on the trail to Pittock Mansion, a romantic hiking destination in Portland, Oregon.Hiking date in progress on the trail to Pittock Mansion.

Pittsburgh – Laurel Highlands Hiking Trail (LHHT) from Ohiopyle State Park

A 90 min drive from Pittsburgh, Ohiopyle is where to catch the LHHT. We’re not gonna attempt the whole trail, which, at 70 miles, is a serious undertaking. For date-purposes, let’s just enjoy the first couple miles, a steep ascent leading to a rocky cliff with a gorgeous view of the Youghiogheny River and beyond. Stop there absorb scenery and likely spot a few river rafters floating lazily on their way, then head back downhill to where you started. Click here for more info on the LHHT.

Hiking date in progress on the Laurel Highlands Hiking Trail in Ohiopyle State Park near Pittsburgh, Pennsylvania. Hiking date in progress on the Laurel Highlands Hiking Trail.

Chicago – The Wooded Island and Phoenix Garden in Jackson Park

Just off Lake Michigan, Chicago’s Jackson Park was created as the grounds for the great Columbian Exposition World’s Fair of 1893 and designed by legendary Central Park landscaper Frederick Law Olmsted. Today, it’s a great green escape from the urban cacophony of the Midwest Metropolis. Grab your boo and stroll its tree-lined paths to The Wooded Island, where you’ll encounter the fantastically serene Phoenix Garden, one of the most prominent remaining features of the historic fair. Find more info here.

The Phoenix Garden in Chicago's Jackson Park.The Phoenix Garden in Chicago’s Jackson Park.

Houston – White Oak Bayou Greenway Trail

To observe Houston’s downtown sparkle from a quiet, green-lined remove, follow your sweetie to the section of White Oak Bayou Greenway Trail off White Oak Drive between Houston Ave and Watson St. Keep an eye out during your swoon-inducing stroll for a natural wetland recently restored to health by a SCA Houston crew comprised of high-school-age youth from the surrounding community. Click here to find the spot.

A view of the downtown Houston skyline from the White Oak Bayou Greenway TrailA view of the downtown Houston skyline from the White Oak Bayou Greenway Trail.

This is page 1. Click here for page 2, where you’ll find date hikes in DC, Seattle, New York, Oakland, and Salt Lake City.

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