Insights & Stories

Autumn Adventure: Road Trip on the East Coast

Reading time: 5 minutes

September 20th, 2023

When it comes to enjoying a vacation, summer may come to mind as the best time to travel. But with the added stresses of more crowded flights, pricier-than-usual hotel rates, and hotter weather during June, July, and August, taking a trip during the summertime has its drawbacks.

Instead, why not consider an autumn vacation? From September to November, discover picturesque landscapes with vibrant seasonal foliage, visit charming towns (and skip the summer tourists). New England is especially beautiful during this time of year with lots of activities—from outdoor adventures, such as hiking and camping, to farmers markets, art and music festivals, and more.

There's no better way to explore the East Coast than on a road trip. And with Hawaiian Airlines® flying directly from can't-miss cities, including Boston and New York City, it's easier than ever to plan a fall getaway. Here's a guide to your next East Coast fall road trip and a few must-see attractions along the way.


Begin your journey by booking a one-way flight on Hawaiian Airlines from Honolulu to Boston, where there's plenty to see and do. The history of Massachusetts' capital dates back hundreds of years, to the time when America was still a collection of British colonies.

Learn more about Boston's pivotal role in early America by walking the Freedom Trail, a 2.5-mile path that loops 17 sites significant to the beginning of the United States, such as Boston Common (America's oldest park established in 1634), the Old North Church (which alerted freedom fighter Paul Revere to British troops' movements), and the Bunker Hill Monument, the site of a pivotal early battle in the American Revolutionary War. For a bite, stop in at historic Faneuil Hall Marketplace, a center of commerce in Boston since the mid-1700s. Enjoy freshly prepared clam chowder and lobster rolls while watching world-famous street performers, including acrobats, jugglers, magicians, and musicians, who perform daily at the marketplace.

From Boston, hit the road! The most scenic route along the coast is Interstate-95, which runs more or less parallel to the Atlantic Ocean. Driving straight through, it's possible to make the drive from Boston to New York City in four hours or so, depending on traffic. But with so many attractions to experience along the way—not to mention spending time in Boston and NYC—that you'll probably want to give yourself closer to a week to enjoy this New England fall road trip.

Take a detour off the highway to Cape Cod along the Massachusetts coast. Normally a summer destination due to its temperate weather and miles of golden beaches, Cape Cod is also perfect in autumn. Visitors can appreciate fewer crowds after Labor Day, warm temps (for New England), and great outdoor adventures. Go kayaking or paddle boarding on one of Cape Cod's many picturesque bays and kettle ponds, or charter a fishing boat to go clamming for your very own catch of the day. You can also let the pros handle the cooking—enjoy fresh shellfish, chowder, and the catch of the day at local hotspots, such as the rustic Impudent Oyster, the stately Beach House Grill, or Brewster Fish House, located in a cozy cottage right off Main Street.

Before you leave the state, don't miss Battleship Cove, America's Fleet Museum in Fall River that features the world's largest assemblage of World War II naval vessels, including the highly decorated battleship USS Massachusetts and the attack submarine USS Lionfish.

Rhode Island

A 30-minute drive from Fall River is Newport, Rhode Island, known for its majestic Gilded Age mansions for famous families, such as the Vanderbilts, Astors, and Kennedys. The largest and grandest of these Downton Abbey-style palaces is the Breakers, a five-floor, 125,000-square-foot “cottage" that was once the summer residence for socialite Cornelius Vanderbilt II. Located on a 14-acre estate, the Breakers has since been converted into a historic house museum that's open daily for self-guided tours. Don't miss this National Historic Landmark or the breathtaking cliffs overlooking Easton Bay and the Atlantic Ocean. For up close views of the bay, continue on to Castle Hill Lighthouse, whose rustic charm has made it a symbol of Newport.


An hour's drive from Newport is the town of Mystic in nearby Connecticut. The Mystic Seaport is the nation's leading maritime museum, whose museum grounds span more than 19 acres on the Mystic River. Attractions include a recreated 19th-century New England coastal village, a working shipyard and 500-plus historic watercraft, such as the 1841 whaling ship Charles W. Morgan, America's oldest commercial ship still afloat. Film buffs may recognize Mystic for its namesake pizza parlor that inspired the 1988 movie Mystic Pizza, which helped launch Julia Roberts' acting career. Stop in for a slice and a selfie at this local hotspot that is celebrating 50 years of business in 2023.

Continue on to Gillette Castle State Park in East Haddam to visit the former home of Sherlock Holmes actor William Gillette, who built this 24-room stone castle in the style of a Medieval gothic fortress. Through the end of September, you can also camp on the estate's 184-acre grounds. Learn more about literal knights—well, the historic Knights of Columbus Catholic fraternity—and the Elizabethan period at the Knights of Columbus Museum and the Yale Center for British Art in New Haven, Connecticut. For dinner, head to Little Italy just east of downtown and follow the smells of bruschetta and ravioli to Consiglio's Restaurant, which makes homemade pasta and the city's best eggplant parmigiana.

New York

There's no better way to celebrate autumn in New England than by visiting Sleepy Hollow in New York's Hudson Valley, the setting of Washington Irving's famous 1820 story “The Legend of Sleepy Hollow." Cross the Headless Horseman Bridge while visiting historic sites from early America, such as the Old Dutch Church and the Sleepy Hollow Cemetery. But it's not all doom and gloom here: The TaSH (Tarrytown and Sleepy Hollow) Farmers Market is held every Sunday morning and the Music Hall in nearby Tarrytown was one of the first theaters in the country to show movies back in 1901. These days, you're more likely to catch performances by The Kingston Trio, Ani DiFranco, and The Grass Roots (who are all performing there this September and October).

From Tarrytown, it's only a 30-minute drive to New York City, where there are too many attractions to list. Check off bucket list items by visiting the Statue of Liberty and the Empire State Building, or take a more relaxed approach and unwind amongst New Yorkers in Central Park, the High Line, and Chelsea Market. Foodies will rejoice at being able to visit an iconic restaurant on nearly every block in New York City, from Central Park's Tavern on the Green to Katz's Delicatessen on the Lower East Side to Peter Luger Steak House over the river in Brooklyn. Art lovers can enjoy priceless works at the Museum of Modern Art, the MET, Guggenheim, and the Whitney, among others. Meanwhile sports fans can catch a game at Madison Square Garden, Yankee Stadium, and Citi Field. In the evening, enjoy a concert at Radio City Music Hall or any number of Broadway shows—from classics, including Chicago and Sweeney Todd, to modern hits, such as The Book of Mormon and Hamilton.

In New York City, it's often tougher to use a car (finding street parking is difficult in a city of nearly 9 million people) compared to traveling by subway, bus, ferry, and any number of rideshare apps, so it's probably easier to ditch your rental car when you first arrive in the city. Use these transportation methods to reach the airport when your trip ends and snag a flight from New York City to Honolulu. No layover necessary—Hawaiian Airlines offers daily nonstop flights.

Ready to start planning your east coast road trip? There's no need to wait! Your everyday purchases can help you earn HawaiianMiles® faster, making that dream trip a reality even sooner! With the Hawaiian Airlines® Bank of Hawaii World Elite Mastercard® or the Bankoh Hawaiian Airlines® Visa® Debit Card, every purchase earns you HawaiianMiles—which never expire.

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