Block Island RI to Woodstock NY Road Trip Guide

Before the automobile, travelers from Block Island to Woodstock would have faced a multi-day schooner and stagecoach ordeal. Today, the route is a well-paved 190-mile drive, taking roughly 4.5 hours without stops. The trip begins at the Block Island Ferry terminal in Point Judith, RI, crosses Narragansett Bay, then slices westward through Rhode Island and Connecticut before climbing into New York's Catskill foothills. Notably, you'll traverse the Old Post Road (US-1) in Connecticut, a historic corridor that predates the American Revolution. This guide covers everything from best stops Block Island, RI to Woodstock, NY to how long to drive Block Island, RI to Woodstock, NY, helping you decide is it worth driving Block Island, RI to Woodstock, NY, and listing things to do between Block Island, RI and Woodstock, NY.

For tips on finding unique experiences along any route, see how to find the best stops and hidden gems between cities.

Road quality is generally excellent, but watch for deer on CT-20 between Barkhamsted and New Hartford, especially at dawn/dusk. The route has no unsupervised mountain passes, but winter weather can make NY-28 slippery. Always carry an emergency kit. For families, the Mystic Aquarium (55 Coogan Blvd, Mystic, CT) is a slight detour (30 min) but worth it. For child-friendly bathrooms and play areas, rest stops on I-91 Southington (milepost 28) have clean facilities. Pets are welcome at most outdoor attractions; however, bring water and waste bags as rest stops may lack pet areas.

• Fatigue management: Take breaks every 2 hours; ideal stops are Hammonasset Beach State Park (CT-81) and Gillette Castle (67 River Rd, East Haddam, CT)
• Hidden off-route spot: The Devil's Hopyard State Park (41.4732°N, 72.3461°W) – a 10-minute detour from CT-82 featuring a 60-foot waterfall and glacial potholes.
• Pet-friendly: The Ashokan Rail Trail (pet-friendly, 3 miles) near Woodstock offers leashed access

For rest, the Welcome Center on I-91 North in Hartford (milepost 34) offers 24/7 restrooms and vending. For a quiet, scenic break, pull into the Riverton Historic District (41.9420°N, 72.9991°W) on CT-20 – a tiny hamlet with a general store and picnic tables by the Farmington River. Children will enjoy the nearby Barkhamsted Lighthouse (actually a schoolhouse) and its 1930s artifacts.

• Must-stop for families: KidsPlay Museum (61 Main St, Torrington, CT) – 15 min off CT-8
• Pet-friendly hike: Saugerties Lighthouse Trail (168 Lighthouse Dr, Saugerties, NY) – 2 miles roundtrip

Leaving the salt-sprayed bluffs of Block Island (41.1856°N, 71.5750°W), the road quickly transitions to the gentle hills of Rhode Island's South County. Near Kingston, the University of Rhode Island's agricultural fields create a pastoral patchwork. As you cross into Connecticut, the Housatonic River Valley offers a dramatic shift with forested slopes and classic New England barns. The final push into New York's Catskills introduces towering oak and maple forests, with the Ashokan Reservoir (41.9408°N, 74.1942°W) providing a shimmering blue backdrop.

• Block Island: Mohegan Bluffs, clay cliffs 200 ft above ocean
• Rhode Island: Narragansett Bay views from Route 1A
• Connecticut: McLean Game Refuge (41.8990°N, 72.7610°W) – 1,400 acres of meadows and woodland
• New York: Catskill Park, 700,000 acres of state land

Local commerce reflects this transition. Block Island's shops sell sailcloth bags and lobster traps. In rural Connecticut, farm stands offer fresh cider and honey. Woodstock's Tinker Street is lined with art galleries and organic eateries. For a taste of regional crafts, stop in at the Woodstock Guild of Craftsmen (34 Tinker St) – their pottery is a direct link to the area's 1970s artisan boom.

• Block Island souvenirs: Block Island Fishworks (custom rods)
• Farm stop: Bishop's Orchards (1355 Boston Post Rd, Guilford, CT)
• Woodstock artisans: Colony Cafe (buttery scones) and Saugerties Antique Center (nearby)

The primary route follows I-95 W from Providence to New Haven, then I-91 N to CT-20 W, connecting to NY-28 N into Woodstock. The estimated driving time is 4.5 hours, but add 2 hours for the ferry crossing and waiting. Gas stations are abundant along interstates, but become sparse in rural Connecticut after exits 70-80 on I-91. Plan fuel stops in Providence or Hartford. Tolls exist on the Rhode Island side of the Newport Pell Bridge (approx $2-4). The route is well-maintained, but watch for construction on I-95 near New Haven.

• Key roads: I-95 W, I-91 N, CT-20 W, NY-28 N
• Total distance: 190 miles (306 km) plus ferry
• Typical driving time: 4.5 hours (ferry: 1 hour crossing + 1 hour wait)
• Recommended fuel stops: Exit 20 off I-95 in Warwick, RI; Exit 29 off I-91 in Hartford, CT