Two-Night Road Trips From New York City and Boston

Two-Night Road Trips from New York City and Boston

The single most useful fact for planning a New York State weekend road trip is this: the Sunday return queue on I-87 southbound from the Adirondacks can add 45 to 120 minutes to your drive if you leave between 15:00 and 18:00. Every route below gives you the specific departure window to avoid that choke point. The page builds each route as a turn-by-turn weekend starting from either New York City or Boston, with drive-time bands for every leg and the season window for foliage, mud, or black flies noted as a shifting range. For any abandoned or ruined site on the route, the page states whether visiting it is legal.

Adirondack Weekend: Lake George, Peaks, and Paddling

Drive And Arrival

This route works best from May into October, when the Prospect Mountain summit road is open and kayak outfitters on Lake George are running. From New York City, drive time to Lake George Village at I-87 Exit 21-22 is 3 hours 45 minutes to 4 hours 30 minutes, depending on your Manhattan departure point and traffic. Skip the Friday evening drive across the Bronx. Leave by 14:00 or after 19:00.

Saturday Summit And Paddle

Saturday morning, hike Prospect Mountain. The trail from the village is 3.0 miles round trip. For a longer climb, take Buck Mountain at 6.6 miles round trip; the trailhead is off Pilot Knob Road. Have lunch 8 miles north on NY-9N in Bolton Landing. Saturday afternoon, rent a kayak from an outfitter in Bolton Landing. The season runs May into October.

Sunday Escape Window

The failure case is Sunday afternoon. The choke point is I-87 southbound between Exit 23 in Warrensburg and Exit 17N in the Newburgh area. Depart Lake George before 14:00 or after 19:00. If you get stuck in that 15:00-to-18:00 window, budget 45 to 120 extra minutes and carry snacks and water.

Catskills Weekend: Giant Ledge, Tubing, and Diner Food

Getting There And Staying

This is a shorter drive from New York City: 2 hours 15 minutes to 2 hours 45 minutes to Phoenicia on NY-28 via I-87. No chain hotels here. Book a motel or cabin in Phoenicia or Shandaken well ahead on Friday mornings. Black flies can be heavy from mid-May into late June. If you are hiking then, bring a head net and long sleeves.

Saturday: Hike, Eat, Tube

Saturday, hike Giant Ledge and Panther Mountain: 6.3 miles round trip from the trailhead on County Road 47, 8 miles west of Phoenicia. The view from Giant Ledge is the payoff. You look across the Esopus Creek valley and the vast, roadless Slide Mountain Wilderness. Lunch at the Phoenicia Diner at 5681 NY-28, open 07:00 to 17:00 daily in 2024. Hours are revised annually, so check before you go. Saturday afternoon, tube the Esopus Creek with Town Tinker Tube Rental. The season runs May into September, but only when water levels permit. Call ahead the morning of your trip.

Sunday Getaway

Sunday, the choke point is NY-28 eastbound between Boiceville and the I-87 interchange. Depart Phoenicia before 13:00 or after 18:00. If you leave between 14:00 and 17:00, budget an extra 30 to 90 minutes.

Maine Coast Weekend from Boston: Portland, Camden, and Lobster

Drive And Base

From Boston, Portland is 1 hour 45 minutes to 2 hours 15 minutes on I-95. Book lodging in the Old Port district, where you can walk to restaurants and breweries. This route is best from June into September, when the lobster shacks and schooner sails are running. Black flies are not a problem on the coast, but expect fog on June and July mornings.

Camden And The Bay

Saturday morning, drive 1 hour 30 minutes north on US-1 to Camden. Hike Mount Battie in Camden Hills State Park: 1.5 miles round trip from the trailhead, or drive the auto road if your group has limited mobility. The summit gives a 360-degree view of Penobscot Bay and the islands. For lunch, find a lobster shack in Lincolnville or Rockport. Season is May into October. Saturday afternoon, take a 2-hour schooner sail from Camden Harbor. The season runs June into September. Book in 2024; the schedule is revised annually.

Sunday Return

Sunday, the choke point is I-95 southbound between the York toll plaza at mile 8 and the New Hampshire state line. Depart Portland before 13:00 or after 19:00. If you leave between 14:00 and 18:00, budget an extra 60 to 120 minutes.

Foliage Weekend: Catskills Instead of Vermont

Why Not Vermont

Most leaf peepers head to Vermont's Route 100. Do not. The I-91 southbound queue from St. Johnsbury to the Massachusetts line adds 90 to 180 minutes on Sunday afternoons. Instead, drive the Catskills. From New York City, the Friday stop is Margaretville on NY-28, 2 hours 30 minutes to 3 hours. The peak color window for this region is early to mid-October, but varies with elevation and weather. The New York State Fall Foliage Report publishes weekly updates; check that before you go.

The Loop

Saturday, drive a 55-mile loop: NY-30 south from Margaretville to Downsville, then County Road 7 (Dry Brook Road) past Seager and Balsam Lake Mountain. This road follows the East Branch of the Delaware River and cuts through dense hardwood forest with excellent color in the peak window. Pack a picnic or grab takeout in Margaretville. No restaurants sit on the loop itself.

Sunday Getaway

Sunday, depart Margaretville before 13:00 or after 18:00 to avoid the NY-28 queue eastbound.

Winter Weekend: Lake Placid and Olympic Trails

The Long Haul

This is the longest drive on the page: 4 hours 45 minutes to 5 hours 30 minutes from New York City to Lake Placid on I-87 to Exit 30, then NY-73. The season runs December into March. Snow tires or all-wheel drive are not optional. Carry a shovel and a blanket in the trunk. The road across Keene Valley can ice over without warning.

Saturday On Snow

Saturday morning, ski cross-country at Cascade Ski Center on NY-73. Twenty kilometres of groomed trails. If downhill is your preference, Whiteface Mountain has 87 trails and a 3.5-mile vertical drop; the season runs late November into mid-April. The 2024 schedule is revised annually. Saturday evening, the Lake Placid Olympic Oval is open to the public for speed skating. Hours vary and are set each year.

Sunday Return

Sunday, the choke point is I-87 southbound between Exit 30 in Keene Valley and Exit 23 in Warrensburg. Depart Lake Placid before 13:00 or after 18:00. If you leave between 14:00 and 17:00, budget an extra 45 to 90 minutes.

Abandoned Places Route: Kingston to Rosendale

Rules Of The Road

This route is for travellers interested in ruins and industrial decay. All stops use publicly accessible roads, trails, or scheduled tours. No fencing is breached and no structures are entered. Friday stop is Kingston at I-87 Exit 19, 1 hour 45 minutes to 2 hours 15 minutes from New York City.

Five Saturday Stops

Stop one: the Hudson River State Hospital grounds in Poughkeepsie. Drive the public roads across the former campus and view the buildings from the road. No trespassing signs are posted. Stop two: the Walkway Over the Hudson, a former railroad bridge now a public state park. Open 07:00 to sunset. Entry is free. Stop three: Bannerman Castle on Pollepel Island, viewable from the Metro-North Hudson Line or by kayak. To land on the island, you must take a guided tour with the Bannerman Castle Trust. Season runs May into October. Book in 2024; the schedule is revised annually. No unescorted landing. Stop four: the abandoned cement mines in Rosendale. The Jo Penney Memorial Park trail passes mine entrances. Stay on the trail. No entry into the mines. Stop five: Widow Jane Mine in Rosendale on the Snyder Estate. This is open for events only. Public access is during scheduled tours by the Century House Historical Society, set each year.

Sunday Getaway

Sunday, depart Kingston before 13:00 or after 18:00 to avoid the I-87 queue southbound.