New England Fall Foliage Road Trip in Massachusetts and Maine

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Summertime shines in New England with white-sand beaches, lobster bakes and sailing trips. But fall is when the area shimmers with colors along with great eats and cozy inns.

Inland and coastal routes put on their New England fall foliage finery, ablaze with apple greens, scarlet reds, oranges and yellows. Pick a route, pack your hiking boots, and make reservations in these fabulous towns from Massachusetts to Maine.

New England Fall Foliage: Massachusetts

Cape Cod and the Islands

The summer crowds have gone home and Cape Cod and the islands welcome you to their year-round charms. On the hooked spit of land known as Cape Cod, you can wend your way from Falmouth to Provincetown along route 28, stopping at quaint towns along the way.

The fall foliage here isn’t as dramatic as what you’ll see further north. But, it has its own charms set against the blues of Cape Cod Bay and the Atlantic Ocean.

For a distinctive stay, AutoCamp Cape Cod in Falmouth invites you to cozy up in a retro, restored Airstream. These are kitted out with amenities and furnishings like what you’d find in a traditional hotel room.

Bicycles are complimentary and you can explore along the Shining Sea Bikeway just at the bottom of the driveway. You’ll ride by cranberry bogs and golden sea grass from Falmouth to Woods Hole.

Alternately, sit back and stare at the trees while you toast marshmallows at your own fire pit. The front desk will provide s’mores kits for your campfire. In case you’re concerned about having enough space inside, you needn’t worry.

The smartly designed Airstreams are reminiscent of a stateroom on a cruise ship. Outfitted with a large shower, double bed and kitchenette, they have plenty of space to stash your carry-ons and duffels. Plan a day ferry to Martha’s Vineyard or Nantucket and enjoy the fall’s crisp sea breezes.

For some solid Cape Cod eats, try the Quarterdeck Restaurant in Falmouth. Here Boston scrod is a traditional favorite along with clam chowder and baked stuffed lobster.  

Other welcoming choices include people-watching fave, Bubalas by the Bay in Provincetown and seafood-centric Mattakeese Wharf on Barnstable Harbor.

Boston

En route north, Massachusetts’s stunning capital makes a convenient stop to give you a dose of history. Also, some hearty eats and pretty park colors. Boston’s Back Bay shines with cobblestones and provides some solid hiking.

Walk up and down the hills behind the Massachusetts State House towards shop-filled Charles Street. Book a room at the luxury Newbury Boston for a true fall indulgence including suites that come with a fireplace (and fireplace butler). Finish the day with dinner at the beautiful Contessa restaurant.

From the hotel, saunter through the Boston Common and Public Garden where flowers and trees are ablaze with color. Then walk along the Freedom Trail marked by red bricks in the center of the city’s historic sidewalks.

Finally, make your way to the Rose Kennedy Greenway. Here you’ll meander through a string of parks before heading across Atlantic Avenue to Boston’s burgeoning Seaport District.

The Seaport is set along Boston Harbor and extends to the art- and tech-filled converted warehouses of Fort Point. This is where you’ll find the ICA, Boston’s Institute of Contemporary Art, as well as the pedestrian-friendly Harborwalk.

Conveniently located amid the restaurants, art galleries and music events of the neighborhood is the new Omni Boston Hotel at the Seaport. The Omni has a variety of dining spots for refreshment, from casual Kestra to the hopping Coquette.

For a great place to watch the Bruins and Patriots, The Omni’s Sporting Club has 12 HD screens rimming the walls and a DJ to keep the spirit up.

Slurping bivalves is a must in Boston and Row 34 will give you a wide variety of oysters to try. Or, visit the Barking Crab, set on a boat on the edge of Fort Point Channel.

If you’re in the mood for a steak or traditional fish meal, Ocean Prime on Pier 4 is a favorite among the after-work set. It’s also a magnet for date night.

The bartenders have perfected classic steakhouse favorites like the Bloody Mary and martini, perfect for an evening warm-up along with Instagrammable temptations like the “smoking” Berries & Bubbles.

Rich lobster bisque, filet mignon with Béarnaise sauce and truffle mac ‘n cheese provide stick-to-your-ribs comfort after a breezy walk along the harbor.

The North Shore and Cape Ann

Set your sights north of Boston to the state’s toniest coastline area, the North Shore. Lovely Route 127 winds north through Beverly, Manchester-by-the-Sea and Gloucester.

Most of the route hugs the shore as you approach Cape Ann. You can drive the entire route in about an hour or make a day of it with numerous stops to get your fall foliage fix.

To capture the New England fall colors of the area, plan some time to explore the grounds of Hammond Castle Museum located a short jog off the road in Gloucester. It’s the striking creation of John Hays Hammond, Jr.

Hammond was an inventor who built a medieval castle to house his collection of historical artifacts. Take a tour and ask to see the “hidden” Prohibition-style wine cellar.

Check the calendar for castle concerts, spiritualism tours and other events. Along the way, you can pick out your own lobster and grab some fried clams at the famous Woodman’s of Essex.

To add a mix of art and delicious eats to your visit, head to Gloucester’s Rocky Neck Art Colony filled with galleries and shops. There you’ll find the lively Studio Restaurant. Ask for a seat on the deck, order a blueberry ale and crab Rangoon, and watch the water taxis that ply Smith Cove.

Your final destination is Rockport, another artist haven with a homey, New England flair. Before resting your head in Rockport at the oceanfront Emerson Inn, take a walk along Bearskin Neck with its many boutiques and art galleries.

Don’t miss Motif #1, a red fishing shack said to be the most-painted structure in the world. Also, the Shalin Liu Performance Center. It’s a striking Second Empire-style structure where you can catch a concert or a show while viewing the ocean through a glass wall.

At The Emerson Inn, ask for a room on the third floor. It’s a bit of a climb, but it’s worth it to get a room with sweeping views of the harbor. At the back of the inn’s yard, to the left of the swimming pool, the somewhat hidden Atlantic Path offers a hike along the rocky coast to Halibut Point.

Meander along, taking in the blue water and the leaf and flower colors along the way. Reward yourself back at the inn with cocktails on the porch or inside at the bar.  

New England Fall Foliage: Maine

Lobsters are still available in the fall in beautiful Maine, and that’s definitely where you want to order them. Jumping off routes 93 and 95, pick up route 1. This winding coastal road passes through small towns filled with quaint homes, lobster ponds, art galleries and historic captains’ residences.

Pause for a while in Perkins Cove, a jog east near Ogunquit, stopping for a lobster in the rough at Barnacle Billy’s. Follow it with a peppermint stick ice cream cone at Jackie’s Sweetside, a true New England treat.

Then set off on one of the state’s most gorgeous walks, The Marginal Way. Take time to savor the New England fall foliage scenery along this path that hugs the dramatic Maine coastline. The views of the cliffs and crashing waves inspired Winslow Homer to create his series of seascapes.

Along the way, you’ll see beautiful flowers and landscaped lawns forming a rainbow contrast to the blue and white of the water below.

Kennebunk and Kennebunkport

The tony Kennebunks, with their stately mansions and Victorian homes, grew initially from the towns’ shipbuilding prowess with homes for the area’s sea captains. Today, the villages are known for their relaxed seaside vibe and famous summer residents, the late President George H.W. Bush and his family.

Driving down tree-lined Summer Street with its grand 19th-century homes is a tour through architectural history. The widows’ walks, multi-colored Victorian homes and yellow and white Wedding Cake House are especially vibrant against the changing New England fall foliage.

Turn onto King’s Highway to beautiful Goose Neck Beach. Here you’ll want to book a room at the yellow-painted The Tides Beach Club.

The beachside boutique hotel has well-appointed rooms and its own restaurant and bar. There is also an inviting rocking chair-filled porch where you can sip a cocktail and admire the changing foliage.

A dreamy drive along exclusive Ocean Avenue leads you to the Bush family estate with a curving seashore drive. For a luxe stay to the tune of ocean waves, book a room at the Cape Arundel Inn and Resort. Then enjoy dinner in the oceanfront restaurant.

For a village-side setting that’s perfect for exploring, the historic Kennebunkport Inn has an outdoor patio for warmer-day dining with live music.  

Outdoor lovers will enjoy Hidden Pond. It’s a cluster of cottages, bungalows and a lodge set in the woods. Plus there’s a variety of hiking trails and the farm-to-fork Earth restaurant.

Portland and Cape Elizabeth

With a rich history in fishing and agriculture, Portland is today regaled as a true foodie city. There are seafood-specialist restaurants like J’s Oyster, a favorite of Anthony Bourdain,  and the floating DiMillos (which sits on a former car ferry). Plus inventive bistros like Fore Street and Central Provisions.

Portland promises that you’ll never go hungry. Choose to drive along Portland’s tony Eastern Promenade with its many beautiful Victorian homes. Or, park and hike the two-mile Eastern Promenade Trail along the harbor for New England fall foliage up close. Rest your head at the centrally located Portland Harbor Hotel and enjoy dining and drinks at the Harbor Bistro + Terrace.

Head east to Cape Elizabeth and enjoy a gorgeous stretch of land where you’ll find one of the best resorts in the state. The Inn by the Sea is just 10 minutes outside of Portland and is a pet-friendly resort.

Here you can satisfy your fall-color hunger with a gorgeously landscaped lawn, planted with the richest and most unusual seasonal florals.

Take a walk down the inn’s private walkway to the beach. Marvel at the rich foliage overhead and alongside as you approach the ocean. For a taste of fall, the resort’s Sea Glass restaurant knows how to do Maine right.

Executive Chef David Brown offers lobster Benedict and oversized blueberry pancakes for breakfast and a meat-packed lobster roll for lunch. Plus, of course, the catch-of-the-day, cooked any way you’d like for dinner. Reservations are suggested.