New England Road Trips for Fall Color

Huttopoia White Mountains courtesy Huttopia White Mountains
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There’s no shortage of destinations to visit in New England to see the brilliant fall colors. Weaving a mosaic of yellows, reds, oranges and greens, leaves and flowers form an oriental carpet of tones in the mountains, in the towns and by the shore. Here are some of my favorite routes in New Hampshire, Massachusetts and Maine where you’re guaranteed photo-worthy stops for good eats, great visuals and relaxing accommodations. 


The White Mountains

New Englanders will tell you that your first road trip to see the area’s best foliage should be along The Kancamagus Highway in Northern New Hampshire. One of New England’s most colorful foliage drives, Route 112 is a slow-go along the 34.5-mile designated American Scenic Byway. Winding through the heart of the scenic White Mountain National Forest, the road affords many vista points over falls and gorges. Just be sure to pack your patience along with your hiking boots.

Overnight in a cabin or tent at Huttopia White Mountains, a glamping resort with a picturesque creek in its backyard near beautiful Iona Lake. For a heady dose of classic New Hampshire, North Conway in Mount Washington Valley is where you’ll find the family-owned, pet-friendly White Mountain Hotel and Resort and the Instagram-perfect Muddy Moose restaurant for burgers, pastas, steak and an extensive brew menu.

Muddy Moose courtesy Muddy Moose

The ultimate route for leaf peepers, the eight-mile Mt. Washington Auto Road lets you summit the nearly mile-high mountain in the socially distant setting of your car. If you don’t want to deal with traffic, you can hike one of the many mountain trails that offer 360-degree views or take the Conway Scenic Railroad from its 1874 train station for a ride through Crawford Notch and Mount Washington Valley. To refuel, park your boots at The Notch Grille for New England comfort food at the Glen House at the base where you can book a room and admire your achievement: earning a bumper sticker that says “This car climbed Mt. Washington” even if you didn’t actually drive the route.

Shalin Liu Performance Center ©Meryl Pearlstein


The colors of Maine add the blue and white hues of the coast to the leafy palate.  Walk inland or along coastal trails where reflections off trees grace the rocky shoreline. Lobsters are still available in the fall, and Maine is till the best place to order them. 

Kittery, Ogunquit and Perkins Cove

Pick up route 1 in Kittery in Southern Maine and follow the road north, winding inland with worthy coastal detours that pass  through small towns filled with lobster pounds, farms, art galleries and stately residences. 

Pause for a while in Perkins Cove near Ogunquit, stopping for a lobster in the rough at Barnacle Billy’s and a peppermint stick ice cream cone at Jackie’s Sweetside, before setting off on one of the state’s most gorgeous walks, The Marginal Way. Take time to savor the scenery along this path that hugs the dramatic Maine coastline – the views of the state’s cliffs and crashing waves inspired Winslow Homer to create his series of seascapes. Along the way, you’ll see beautiful flowers and landscaped lawns, all forming a rainbow-like contrast to the blue and white of the water below.

The Marginal Way courtesy Visit Maine

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-cenutry 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 fall leaves. 

Captain’s House Summer Street, Kennebunk ©Meryl Pearlstein

Turn onto King’s Highway to beautiful Goose Neck Beach where you’ll want to book a room at the yellow-painted The Tides Beach Club. The beachside boutique hotel has well-appointed rooms, its own restaurant and bar, and a gorgeous rocking chair-filled porch where you can sip a cocktail and admire the waves and the changing foliage. 

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

Cape Arundel courtesy Visit Maine

For a more village-side setting that’s perfect for exploring, the Kennebunkport Inn has an outdoor patio for warmer-day dining with live music.  Outdoor lovers will enjoy Hidden Pond, a cluster of cottages, bungalows and a lodge set in the woods with 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. From seafood-specialist restaurants like Scales and DiMillos (which sits on an actual ship) to 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. 

Then head east to Cape Elizabeth, a gorgeous stretch of land where you’ll find one of the best resorts in the state, The Inn by the Sea. Just 10 minutes outside of Portland, the luxe, pet- and family-friendly resort will satisfy your fall-color hunger with its gorgeously landscaped lawn, planted with the richest and most unusual florals of the season. Take a stroll down the private walkway to the beach, marveling 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 Andrew Chadwick offers oversized blueberry pancakes for breakfast, a meat-packed lobster roll for lunch, and, of course, the catch-of-the day, cooked up any way you’d like for dinner. Reservations are suggested.

Inn by the Sea courtesy Inn by the Sea


Cape Cod, Nantucket and Martha’s Vineyard

The summer crowds have left and this is a glorious time to visit Cape Cod and the islands. On the hooked spit of land known as Cape Cod, you can wend your way from Falmouth to Provincetown along route 28, stopping at the quaint towns along the way. The foliage here isn’t 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 kitted out with amenities and furnishings similar to what you’d find in a traditional hotel room. Bicycles are complimentary and you can explore along the Shining Sea Bikeway at the bottom of the driveway, riding by cranberry bogs and golden sea grass from Falmouth to Woods Hole. Or sit back and stare at the trees while you toast marshmallows at your own fire pit — the front desk will provide a s’mores kit for your campfire. In case you’re concerned about having enough space inside, you needn’t worry. The smartly designed Airstream is reminiscent of a stateroom on a cruise ship with a large shower, double bed, kitchenette and 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.

Shining Sea Bikeway ©Michele LeCamera

For some solid Cape Cod eats, try the Quarterdeck Restaurant in Falmouth, where Boston scrod is a traditional favorite along with clam chowder and baked stuffed lobster.  Other welcoming choices include peoplewatching fave Bubala’s by the Bay in Provincetown and seafood-centric Mattakeese Wharf on Barnstable Harbor.

Lobster, a New England specialty ©Meryl Pearlstein


En route north, Massachusetts’s stunning capital makes a convenient stop to pick up a dose of history along with some hearty eats and pretty park colors. Boston’s Back Bay shines with cobblestones and provides some solid hiking up and down the roads of Beacon Hill  behind the Massachusetts State House.

Book a room at the luxury Newbury Boston and enjoy a true fall indulgence, a suite with a fireplace  and your own fireplace butler, and 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, walk along the Freedom Trail marked by red bricks in the center of the city’s historic sidewalks, and make your way to the Rose Kennedy Greenway where you’ll meander through a string of parks before heading across Atlantic Avenue to Boston’s burgeoning Seaport District

Public Garden ©Kyle Klein Photography

Set along Boston Harbor and extending to the art- and tech-filled converted warehouses of Fort Point, the Seaport 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, the new Omni Boston Hotel at the Seaport 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 Sporting Bar has 12 HD screens rimming the walls. 

Slurping bivalves is a must in Boston and Row 34 will give you a broad 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 a more substantial seafood meal, Ocean Prime on Pier 4 is a favorite among locals and the after-work set. The bartenders have perfected classic steakhouse cocktails like the Bloody Mary and martini, perfect for an evening warm-up, along with new Instagrammable temptations like the “smoking” Berries & Bubbles. Rich lobster bisque, filet mignon, and truffle mac ‘n cheese provide stick-to-your-ribs comfort after a breezy walk along the harbor.

Ocean Prime ©Meryl Pearlstein

The North Shore

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 with most of it hugging 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 foliage fix. 

To capture the colors of the area, plan some time to explore the grounds of Hammond Castle Museum, located near the Manchester-Gloucester border. It’s the striking creation of John Hays Hammond, Jr., 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.

Never forgetting that you’re traveling along the coast, you can pick out your own lobster and grab some fried clams at famous Woodman’s of Essex, a short ride away. To add a mix of art and delicious eats to your visit, head to Gloucester’s Rocky Neck area filled with galleries and shops. There you’ll find the lively Studio Restaurant and Bar. Ask for a seat on the deck, order a blueberry ale and crab Rangoon, and watch the water taxis that ply the harbor.

Hammond Castle Museum courtesy Aakash Arun

Your final destination is Rockport, an artist colony with a homey, New England flair. Before you rest your head in Rockport at the oceanfront Emerson Inn, take a walk along Bearskin Neck with its many shops and art galleries. Don’t miss Motif #1, a red fishing shack said to be the most-painted structure in the world, and the Shalin Lui Performance Center, a striking Second Empire style structure where you can catch a concert or a show while viewing the ocean through a glass wall. 

Motif #1 ©Meryl Pearlstein

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 Pigeon Cove. At the back of the inn’s yard, the somewhat hidden Atlantic Path offers a sedate hike along the rocky coast to Halibut Point. Meander along, taking in the blue of the water and the varied tree and floral colors along the way. Reward yourself back at the inn with cocktails on the porch or inside the bar.  


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