There’s something special about a road trip that starts right from your own driveway. No airport security, no luggage fees—just pile in the car, cue up the playlist, and go. This year, we set our sights on the Northeast with one ambitious goal: hit every state in the region. What unfolded over the next several days was a mix of American history, stunning coastal scenery, and the kind of spontaneous detours that make family travel so memorable.
This post covers the first two days of our adventure—the long haul from home to Plymouth, Massachusetts, with stops in Newport, Rhode Island, and Salem along the way.
Day 1: The Long Haul North
We hit the road at the crack of dawn, coffee in hand and Plymouth, Massachusetts, firmly in our sights. If you’ve ever driven I-95 through the mid-Atlantic corridor, you know the drill: tolls, traffic, and more tolls. We pushed through Virginia, Maryland, New Jersey, and New York with the determination of a family on a mission.
The early miles weren’t exactly scenic—highway driving rarely is—but once we cleared New York, we made a decision that changed the whole vibe of the trip. We ditched the interstate and took the coastal route instead.
Newport, Rhode Island: A Quick But Memorable Stop
By late afternoon, we found ourselves in Newport, Rhode Island, with stiff legs and growling stomachs. We’d planned this as a quick stretch-your-legs stop, but Newport had other plans for us.
We walked a portion of the famous Cliff Walk, a 3.5-mile path that hugs the coastline and passes by some of the most jaw-dropping mansions you’ll ever see. These were the summer “cottages” of America’s Gilded Age elite—the Vanderbilts, Astors, and their contemporaries. The weather was very New England—cloudy, a bit damp—but honestly, it added to the moody atmosphere. The views of the Atlantic crashing against the rocks below were absolutely stunning.
For dinner, we grabbed a table at The Wharf, a casual coastal seafood spot right on the water. After hours in the car, fresh seafood and ocean views were exactly what we needed.
From there, it was a straight shot to Plymouth and our hotel for the night: the John Carver Inn and Spa. Pro tip for traveling with kids—this place has an incredible pool with a Pilgrim theme (yes, really) and an arcade. We made sure to arrive with enough time to let the kids burn off some energy before bed. Worth every minute.
Day 2: Plymouth, Beaches, and Salem
The kids were up early, eager for more pool time before checkout. After they got their fill, we headed to Water Street Cafe for breakfast. This place was quintessential small-town New England—cozy, welcoming, complete with a table of church ladies catching up over coffee and eggs. The food was delicious and the vibe was perfect.
Exploring Plymouth
After breakfast, we walked into downtown Plymouth to soak up some American history. The highlight? Watching the Mayflower II set sail. We happened to be there at just the right moment, and seeing this replica ship head out into the harbor was genuinely moving.
Of course, we had to visit Plymouth Rock. And yes—if you haven’t been, prepare yourself. It’s… small. Like, really small. But there’s something meaningful about standing at the spot where this country’s story began, even if the rock itself is underwhelming.
The kids walked out along the sea wall for a different perspective while we strolled through the waterfront gardens and popped into a few shops. It was relaxed and unhurried—exactly what we wanted.
Wingaersheek Beach: A Hidden Gem
From Plymouth, we made a push north to Wingaersheek Beach in Gloucester. Because it was early in the season, we had the entire beach practically to ourselves. During peak summer, this spot requires parking reservations, so our timing was perfect.
We spent a few glorious hours exploring. The kids discovered tidal pools teeming with crabs and other marine life, climbed on the rocks jutting out into the water, and just ran wild on the sand. It’s the kind of beach that invites exploration—not just sunbathing.
An Audible to Salem
By mid-afternoon, we were hungry and realized we were close to Salem, Massachusetts. We called an audible and decided to stop on our way to Portland.
Salem turned out to be a fantastic surprise. We parked and did our own self-guided walking tour through town. We wandered through the old cemetery, checked out the Witch Museum, and grabbed ice cream to fuel the exploration.
For dinner, we stumbled upon Longboard’s Bar—a laid-back spot with great food and cold drinks. It was the perfect way to end a day packed with adventure.
With full bellies and tired kids, we hopped back in the car for the final push to Portland, Maine. Our Fairfield Marriott awaited, and the next morning we’d finally arrive at Acadia National Park—but that’s a story for the next post.
Tips & Info
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I-95 Tolls: Budget for tolls if you’re driving through the mid-Atlantic. They add up quickly, especially through New Jersey and New York. Consider an E-ZPass to keep things moving.
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Newport Cliff Walk: Free and open to the public. The full walk is 3.5 miles, but you can easily do shorter sections. Wear sturdy shoes—some portions are rocky.
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The Wharf, Newport: Great casual seafood with water views. wharfcoastalseafood.com
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John Carver Inn, Plymouth: Excellent for families. The themed pool and arcade make it more than just a place to sleep. johncarverinn.com
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Water Street Cafe, Plymouth: Cozy breakfast spot with small-town charm. waterstreetcafeplymouthmass.com
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Wingaersheek Beach: In summer, parking reservations are required. Early season visits mean more space and no crowds. discovergloucester.com
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Salem: Give yourself at least 2-3 hours to explore. The Witch Museum is family-friendly and offers good historical context beyond the spooky stuff.
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Longboard’s Bar, Salem: Casual dinner spot with solid food. longboardsbar.com
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Pacing: Don’t try to do too much in one day. We intentionally built in beach time and flexibility, which made all the difference for traveling with kids.