Scenic overlooks on either side allow travelers to stop and take in the expansive view of Port Jervis, the lower Neversink valley and adjacent regions of Pennsylvania.

These give way to wooded areas eventually broken by fields in Wawayanda where Route 6 crosses over again to merge with NY 17M and recross at exit 15, the first of two that serve the city of Middletown.

This junction is the western corner of Orange County's "golden triangle" of Interstates, so-called for its attractiveness to businesses for their distribution centers.

[5][6] Immediately afterward I-84 passes between the Galleria at Crystal Run, the county's largest mall, and the eponymous office park to the south.

The tracks of Metro-North Railroad's Port Jervis Line runs just north of the highway for a short distance, and NY 211 also parallels for several miles past the hills of Highland Lakes State Park.

In the area is a Staples warehouse[9] north of the Interstate along NY 208 and numerous distribution centers (Home Depot, Do-it-Best and others) and truck terminals (including UPS, FedEx and 3 others), along an adjacent roadway on the south side.

The freeway resumes its eastern heading again and descends a gentle slope to its junction with the New York State Thruway (I-87) and NY 300.

Traffic was routed to the Thruway via a short section of 300 when the Interstate was built, but a major project to build a connector directly to the toll road was completed in December 2009, after being under construction for five years.

A mile and a half (2.4 km) east, US 9W and NY 32 provide the last exit before the road crosses the Newburgh–Beacon Bridge, with views of Newburgh Bay and the Hudson Highlands to the south.

I-84 bends through the lowlands north of Sour Mountain, northern end of the Hudson Highlands, and crosses Fishkill Creek.

[17] From there it descends gently over two miles (3.2 km), with Hosner Mountain looming to the east, to the sprawling interchange with the Taconic State Parkway.

After a quarter-mile-long (400 m) bridge over the Croton River, US 6, US 202 and NY 22 just north of Brewster, the Interstate returns to its eastern heading for the northern terminus of I-684, an exit that also provides access to the other three highways.

US 6 and US 202 closely parallel I-84 to the north, between the freeway and one of the upper basins of East Branch Reservoir, part of New York City's water supply system.

Two miles (3.2 km) to the east, Signs appear for Saw Mill Road, exit 1 on Connecticut's stretch of I-84, and its ramps leave the highway just a hundred feet (30 m) before the state line.

In 1959, it looked it would be delayed again when the federal funding formula was changed and less money was available, making a four-lane bridge too expensive to construct.

[18] Construction began in 1960 after the new governor, Nelson Rockefeller, promised to expedite it during his campaign by building a single span, within the limits of what the state could afford without federal aid.

[2] The Newburgh–Beacon Bridge crossed nearly two miles (3.2 km) of Newburgh Bay and led to the last run of the original Newburgh–Beacon Ferry the day after it opened.

The rest of the route would be slowed by both the hilly terrain and local resistance over what was felt to be inadequate eminent domain payments to affected landowners.

Around that time the two agencies also announced plans, and received federal funding, to redo the current exit 36 allowing traffic to go directly between I-84 and the Thruway instead of using a short stretch of NY 300, which by then was more heavily developed than it had been when the Interstates were first built.

Local road Drury Lane was upgraded and widened into newly designated NY 747 to allow easier access to Stewart International Airport via an almost-full diamond interchange.

The Thruway Authority's involvement with the road would have ended in 2006 when its board voted to transfer the highway back to the state DOT, a move it suggested did not commit it to doing so.

But residents of the mid-Hudson region felt NYSTA had done a better job plowing the road in winter, and Thruway workers assigned to I-84 feared having to move or working for the DOT at lower pay and with different union representation.

[23] State Senator John Bonacic, a member of that body's then-Republican majority whose district covers western Orange County, introduced legislation at the beginning of 2007 to block the changeover.

He succeeded, as the budget lawmakers and new governor Eliot Spitzer agreed to appropriate enough money for DOT to continue paying the Thruway Authority for snow removal, litter pickup and mowing along the entire highway save the bridge.

With the state facing financial difficulties in the slow economy, Governor David Paterson decided that DOT could save a few million dollars doing the work itself.

In August of that year, the department bought $6 million worth of new equipment and hired 54 new employees to handle maintenance duties on the highway.

[31] Also in 2019, the exits were renumbered from sequential to mile-based as part of a sign replacement project by NYSDOT, in accordance with MUTCD regulations.

Aderson, an assistant superintendent at the Valley Central School District in Montgomery, was returning to his LaGrange home on the evening of February 5, 1997, when he had a minor collision with a relatively new green Jeep Cherokee carrying what appeared to be New Hampshire license plates just before crossing the Newburgh–Beacon Bridge.

A police sketch based on Aderson's description has been widely circulated and is still posted prominently in kiosks at the freeway's rest areas.

On September 21, 2023, a chartered bus carrying ninth-grade members of the Farmingdale High School marching band from Long Island to a weekend at a camp in Pennsylvania suffered a tire failure along westbound I-84 in Wawayanda near Slate Hill and rolled down a 50-foot (15 m) slope into the highway's median strip.