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Take the Train to the Trail.

The Hudson River’s never out of your sight for long on this day-long trip to the Highlands.  The two towns bookending the hike couldn’t be more different: Tarrytown, once home to more than 20 antique shops, is now lined with fast-casual eateries and coffee lounges.  By contrast, Garrison, in the Hudson Highlands, reminds me of a one-road town in the French countryside, silent except for the burble of a little fountain at the only intersection.

First Stop: Tarrytown

In Tarrytown, everyone gets a view of the river, pit bulls pull their little-old-lady masters down the street or loll on the sidewalk while the shopping gets done, and the local delicacy is something called a lubin.  You’ll hear every European and Asian language spoken on the street, because the EF (English First) language school is just up the hill, under a Florentine dome.  The New New York Bridge’s span across the widest part of the Hudson (the Tappan Zee) is more than halfway finished; when complete, you’ll be able to bike across the river to arty Nyack.

1. Buy a round trip ticket from Grand Central Terminal to Tarrytown. (Tip: If you’re traveling in a group, take advantage of the group rate on Metro-North.)  (Tip: Make sure you sit on the west side of the train for good views of the river.  The scenic nature of the train trip along the Hudson make it worth the price of the ticket alone.)
2. Get off at Tarrytown.  If you’re bringing an energetic dog who needs to stretch, exercise him at the park between the train station and the Hudson River before heading uphill into town.
3. Go directly up the hill from the river on South Depot Street.  In just a block or two, the shops along Main Street start.
4. There are three great coffee shops in town, but Muddy Water wins the prize for best for settling in for a long morning with a delicious brew. Besides warm and cold beverages, they have decent baked goods, soup, pie, and hummus.  The shop is comfortable and friendly.
5. You can pick up a take-out lunch at Bella Roma, across the street.  It’s an average, small italian deli.  There’s also a number of sandwich shops and fast-casual places.  For a nice picnic selection, try the shelves at Mint, a gourmet food store and restaurant just up the hill near the Music Hall.  Old world cheeses, crackers, olives, and other italian specialties go great in the backpack.
6. Return to the Tarrytown train station around noon, and get a round-trip ticket to Garrison.

Main Street, Tarrytown.

Next Stop: Garrison

The train groans and sashays up the river, through the smaller “river towns” of the Hudson; watch for old bathhouses and mansions, the riverside walking path that weaves in and out of view as you head north, the prison at Ossining — the train runs right through “Sing Sing”.  In Peekskill, the track makes an almost 90-degree turn to the west, the bend in the river that signals the start of the Highlands.  Peaks rise up, and the towns settle down.  Watch for bald eagles, and fall in love with the Hudson Highlands. Garrison is the first stop after the train skirts under the towering Bear Mountain Bridge.  For such a tiny train station — there’s not even a proper building, or a bathroom — it will be lively on the weekend, when taxi drivers shouting “West Point! West Point!” vye for the fares of returning cadets. The hike leaves from the southeast side of the parking area.

The Hike: Arden Point and Glenclyffe

Features: Views, ruins, history, near train station, one mile from cafe.  Easy, mossy, hardwoods and scattered hemlock and pine.

Get Hiking: From Garrison train station, follow blue-blazed trail.  At the southeast corner of the commuter parking lot, you’ll see the sign for the Arden Point Trail.  This is the start.

Use the map to follow the blue blazes through the woods, past the ruins of a lock factory on the right, and shortly you’ll get to the steel bridge crossing the train tracks.  Cross the bridge, still following the blue trail as it turns right.

Arden Point is a lovely vista at the far north end of the point, with a mossy landing for lunch, with views toward both Garrison’s Landing on the eastern shore and impressive West Point on the west.

Watch for: Hotel Thayer at West Point (large brick building across the river); mile-long freight trains on the western side of the river; Bear Mountain Bridge.

Pick up the Glenclyffe Loop (1.8 miles):  Once across the steel footbridge again, turn right to pick up the red-blazed Glenclyffe Loop.  You’ll walk past a former Capuchin Franciscan monastery, now the Garrison Institute, a multi-faith nonprofit organization. Another building—a 34,000 square foot former dormitory—is used by the Philipstown Department of Recreation.  Multiple vistas of the Hudson River are your reward for this loop that ends back at the train station.

Back at Garrison’s Landing

The only shop you’ll find at Garrison’s Landing, the lonely street of houses right next to the train station, is an antiquarian map store, that’s sometimes open, but mostly not.  But visit the park that’s between the houses and the river, and enjoy the solitude.  This is a town that, to me, seems like it was put under a spell years ago.  It’s quiet, empty, and enchanting.

If you have the energy, it’s a .9-mile walk uphill to Garrison Cafe, one of the best eateries in the area.  They have terrific, fresh salads and sandwiches, creative hot menu items as well as a stellar breakfast.  You can also pick up Trail Conference trail maps there.  To get to the cafe, follow Lower Station Road uphill to Route 9D, then turn left and follow the road to the cafe on the left.

…and head back home.

The trains from Garrison run about once every forty-five minutes back south to New York City.  You can get off the train at Peekskill to have dinner at the popular (and highly-recommended) Peekskill Brewery, a creative brewpub right by the train station there.

Or, get off at Tarrytown again; it’s hard to go hungry there.  One of my favorite gastro-dives is Little Bs (closed on Tuesdays!) for Doc’s cider, sensational burgers, truffle fries, wings and a decent selection of local craft beer and bourbons.  Or, if it’s summer and you really want to do it cheap, join the crowd on the pier at the Washington Irving Boat Club (open to the public) for bad fried food and gin and tonics in a plastic cup, while watching the construction of the new bridge and the sun setting in the gorgeous western sky.

It’s all right there.

Map for Arden Point hike, showing trails. Start at the top (in the train station) and follow the blue blazes south and across the bridge. Loop around Arden Point on red-blazed trails, then cross over the bridge again to continue on the trail through Glenclyffe. If you have the time and energy, more trails can be followed by crossing Route 9 and following the blue-and-red blazed trails to the top of Caste Rock or Sugarloaf Hill.