Walkway Over the Hudson to Hudson Valley Rail Trail

Stellar views, a serene nature area, and a bustling downtown make this journey memorable. Sure, you can ride straight through for a power workout, but we prefer to stop and smell the coffee.

Poughkeepsie to Highland

Walkway, 1.28 miles; paved
Hudson Valley Rail Trail, 4 miles; paved

Our homebase is Walkway Over the Hudson State Historic Park. In case you missed the hoopla, The Walkway is a 19th-century railroad bridge transformed into the world’s longest elevated pedestrian park. For decades, it was a major rail corridor for both freight and passengers, but sat unused after a fire in 1974. In 2009, the revamped bridge reopened for the public, drawing ever-growing crowds, with a 22 percent boost in visitors in 2016 alone. Sure, they come for the stunning views, but also because the span connects to paved rail trails on both sides of the Hudson — Dutchess Rail Trail on the east and Hudson Valley Rail Trail (HVRT) to the west. The latter will be our focus as it weaves through Highland and the Town of Lloyd, following the old New York, New Haven, and Hartford line.

You can park on either side of the river. (East side: Dutchess Rail Trail off Parker Ave/9G (Poughkeepsie). West side: Hudson Valley Rail Trail at Haviland Rd (Highland).

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10 a.m.

Start in Poughkeepsie. At Lola’s, just steps from the Walkway’s Washington Street entrance, pick up a Baja Chicken Wrap (loaded with melted cheddar jack and avocado) for a picnic at one of the scenic spots along the route.

photo by Jeremy Intonti

11:30 a.m.

Take your time crossing the Walkway, stopping to admire the view (that’s CIA to the north), watch boaters, and catch a summer breeze. When you eventually enter the HVRT, look for the shortcut to Vineyard Avenue in Highland. Roll your wheels into a bike rack, and take a java break at Underground Coffee and Ales. If you’re in the mood for breakfast, try the egg-and-avocado Rail Trail Sandwich or a burger (including veggie black bean) and fries with house-made cheese sauce, and the popcorn of the day. Next door, see art, munch on the daily cheese plate, and sip vino at Knaus Gallery and Wine Bar. Located on the same strip, El Paso Mexican is another local favorite, known for its hearty breakfast burritos and tasty tacos served on corn tortillas with lime and onions.

Browse before getting back on your bike: a quick left onto Milton Avenue takes you to Aphrodite’s Antiques + Gifts, a curiosity shop brimming with Victoriana, busts, china, linens, vintage books, and retro jewelry.

2:30 p.m.

Back on the trail, pedal deeper into Ulster. If you toted a picnic lunch from Poughkeepsie, enjoy it either at the Highland Rotary Pavilion, where you’ll encounter a 1915 caboose to remind you of the trail’s origins, or continue onward, passing through the Black Creek Wetlands (you can descend to the creek by steps and picnic there). The trail ends at Tony Williams Park, where you can dine under a sheltered pavilion.

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4:30 p.m.

When it’s time to turn back, keep the kids motivated with the promise of a slice, sub, or panini at Pomod’oro Pizza Café, just before the Walkway. Right next door you’ll find hard and soft ice cream at Frozen Caboose. After crossing back over the river, you can also sit down to a proper meal at CIA-grad-owned Crave Restaurant and Lounge (near the Washington Street Walkway stairs), a foodie destination known for intriguing flavor combinations like broccolini Caesar salad and crab avocado toast. End the day on a sweet note with peanut butter mousse with Concord grape sorbet — you’ve earned it!

Trail Info: www.walkway.orgwww.hudsonvalleyrailtrail.net

Stay in the Loop

For those on foot, take the 3.6-mile Walkway Loop as an alternative. It’ll give you access to a staircase alongside the Mid Hudson Bridge, past beautiful Franny Reese State Park (another 2.5 miles of nature trails), and then back over the Mid-Hudson Bridge by a pedestrian/bicycle route. Here’s the link to see how it works: https://parks.ny.gov/parks/attachments/WalkwayOverHudsonWalkwayLoopTrailBrochure.pdf

Photo taken at the Discover Hudson Valley Ride provided by Gameface Media

Pit Stops

131 Washington St, Poughkeepsie
845.471.8555 ; www.lolascafeandcatering.comUnderground Coffee and Ales 
74 Vineyard Ave, Highland
845.834.3899; www.undergroundcoffeeandales.com

Knaus Gallery and Wine Bar
76 Vineyard Ave, Highland
845.834.3144; Find them on Facebook

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El Paso Mexican 
78 Vineyard Ave, Highland

Aphrodite’s Antiques + Gifts
11 Milton Ave, Highland
845.691.8033; www.aphroditesantiques.comPomod’oro Pizza Café
6 Haviland Rd, Highland
845.834.3838; www.pomodoropizzacafe.com

Frozen Caboose
15 Haviland Rd, Highland
845.834.3774; Find them on Facebook

Crave Restaurant and Lounge
129 Washington St, Poughkeepsie
845.452.3501; www.craverestaurantandlounge.com


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