Hudson Line (Off-peak round-trip $30)
When you’ve tired of MoMA’s lines and admission price, head 80 minutes north to Dia:Beacon (3 Beekman St; 845-440-0100, diabeacon.org. $10). Founded in 1974 and housed in a former Nabisco factory, the Dia (as the cool kids call it) has a vast collection of larger-than-life modern art—Donald Judd’s steely monoliths and Louise Bourgeois’s sinister sculptures—the likes of which conventional museums can’t accommodate for lack of space. Grab lunch in the café or better yet, pack a picnic to enjoy on the sprawling grounds, perched on the edge of the Hudson River. Beware: By the end of the day, you’ll fancy yourself an art critic. You’re not.
— Erin Wylie
Harlem Line (Off-peak round-trip $27.50)
You’ll want your Schwinn for this trip: The Harlem Line terminates at Wassaic, and gives way to the leafy Harlem Valley Rail Trail, a biker’s paradise (visit mta.info for bike-permit guidelines). The gentlest pedal is up to quaint Millerton, where tea at Harney and Sons (13 Main St, 518-789-2121) and a glassblowing experience at Gilmor Glass (2 Main St; 518-789-8000, gilmorglass.com. Call ahead for schedule) will let you catch your breath. A longer detour up a steep, partially paved road to Cascade Mountain Winery (835 Cascade Rd, Amenia; 845-373-9021, cascademt.com) may test just how tipsy you can be without needing training wheels. Find maps and bike tours at hvrt.org or dutchesstourism.com.
— Allison Williams
Hudson Line (Off-peak round-trip $15)
Maybe it’s the Art Deco marquee on the Tarrytown Music Hall, but Main Street in this riverside village, just steps from the train, is almost painfully retro. You can browse antique stores and cluttered boutiques like Whimsies Incognito (52 Main St, 914-631-3355), or grab a coffee from Coffee Labs Roasters (7 Main St, 914-332-1479), an aptly named café that also caters to the family dog. Get your Washington Irving on by hopping a $4 cab to nearby Sunnyside, the “Legend of Sleepy Hollow” author’s onetime estate (150 White Plains Rd; 914-631-8200, hudsonvalley.org).
— Marisa LaScala
New Haven Line (Off-peak round-trip $19.50)
Lazy summer days are for wimps—burn off your winter weight with a vigorous day aboard a kayak in the Norwalk Islands of Connecticut. The night before heading out, stop in The Small Boat Shop (144 Water St; 203-854-5223, thesmallboatshop.com. Give them a call, they’ll pick you up.); you’ll need to be ready to paddle at 9am for a daylong tour ($95). A guide will wind a path between Shea, Grassy and Sheffield Islands, taking a break at the Sheffield Island Lighthouse (123 Water St, 203-838-9444). A lunch stop on one of the islands affords even more breath-catching time before heading back to the mainland by 3:30 or 4pm.