Total distance (approximate): 180 miles (km)
Total driving time (approximate): 4 hours 23 minutes
Recommended number of traveling days: 2
Distance: 3 miles (4.8 km) | Travel time: 13 minutes. Breakfast at Clinton St. Baking Company is as American as apple pie (or blueberry pancakes) – and draws lines that are almost as famous as the food. Looking for a hearty breakfast to fuel your trip? Order a stack of pancakes topped with Maine blueberries and warm maple syrup plus the fried chicken and waffle.
Distance: 7.4 miles (11.9 km) | Travel time: 39 minutes. Randall’s Island is a nature lover’s oasis even though it’s technically a part of Manhattan. It’s surrounded by Harlem River to the west and the East River to the east, comprises miles of waterfront paths, various gardens, and even a sustainable farm. Road trippers can stretch their legs and get a taste of what’s to come at the island’s Randall’s Island Park.
Distance: 30.4 miles (48.9 km) | Travel time: 42 minutes. One state down, two to go. With its single-street downtown lined with mom-and-pop shops, Old Greenwich makes for an ideal pit stop in Connecticut. In this all-American neighborhood dating back to 1640, visitors can do some shopping or simply snag a cup of coffee before watching the boats from Tod’s Point, a picturesque lookout hosting Greenwich’s community sailing club.
Distance: 5.5 miles (8.8 km) | Travel time: 19 minutes. Drivers can relax at Greenwich’s Homestead Inn–Thomas Henkelmann, a boutique hotel with a four-star contemporary French restaurant. The building sits on Rhode Island’s famous Bellevue Avenue, which is lined with 19th-century buildings. For dinner, we recommend any of Henkelmann’s duck creations paired with an award-winning wine and a good night’s sleep.
Distance: 6.7 miles (10.7 km) | Travel time: 21 minutes. Get a taste of authentic New England fare at Fish Restaurant + Bar. Seafood dishes shine at this Stamford favorite, where brunch options include panko-crusted lobster mac and cheese, tuna carpaccio flat bread, and diners’ choice of pan-seared, grilled, or blackened fish. Our advice: opt for an everything bagel crusting.
Distance: 61 miles (9.6 km) | Travel time: 1 hour 34 minutes. Hammonasset Beach State Park is the largest shoreline park in Connecticut that offers plenty to do for nature enthusiasts. It has two miles of beachfront along the Long Island Sound, over 550 campsites, hiking and biking trails, and opportunities to fish and picnic.
Distance: 84.8 miles (136.4 km) | Travel time: 1 hour 34 minutes. Want an Instagram shot that lets everyone know that you’ve been to Newport? No Newport site says “wish you were here” more loudly than Newport Bridge. The 49-year-old Claiborne Pell Bridge, known locally as the Newport Bridge, has become an iconic symbol of the Rhode Island town. It even has its own hashtag: #ThatNPTBridge.
Distance: 9.2 miles (14.8 km) | Travel time: 21 minutes. Celebrate the end of your trip with a toast. Stretch your legs while you stroll around the 75 acres of preserved farmland at Newport Vineyards. Relax with a glass of estate-grown wine, or tour and eat on the property.