I've always wanted to visit New England in the Fall. The region is a treasure trove of iconic American experiences, from colonial cities to rocky bays and forested peaks. Whether planning a fall trip or a summer vacation, destinations like Boston, Portland, Cape Cod, and Bar Harbor promise unforgettable memories - each with their own local flavor and unique attractions.
Vacations by Rail have a number of tours that cover this incredible part of the USA. On a recent trip in late September, I visited some key destination highlights and met many of our hotel partners.
The flavors of historic Boston
Boston masterfully blends American history with contemporary charm. I walked the cobbled streets along the Freedom Trail starting at the far end in Charlestown. The city is clean, laid-back and full of museums, galleries, top-rated seafood restaurants, and some incredible breweries. A personal highlight was Trillium Garden on The Greenway in the financial district and their nearby brewery in Fort Point.
I loved the Italian North End and went on a great food tour with Bobby from North End Boston Tours, learning about the history of the area through his own experiences, interlaced with some stunning food. A must is Mike's Pastry, well worth the queues to sample an enormous cannolo.
Boston's waterfront is pulsing with activity, and neighborhoods like Back Bay overflow with shopping and dining for every taste.
Rhode Island and Cape Cod: Classic coastal scenes
As Rhode Island's capital, Providence brims with trendy restaurants, riverside walks and a vibrant arts scene. WaterFire's dramatic river bonfires are a local highlight. I enjoyed walking round the city's own freedom trail. A brilliant place to go, in a very cool downtown area, is the Malted Barley. Their gourmet bagels are a joy, washed down with a small flight of beer from the collection of craft beers on tap.
In Newport, soak up Gilded Age splendor while wandering past the storied mansions, or stroll the Cliff Walk for panoramic ocean views. Both cities offer visitors a mix of relaxation, culture, and beautiful scenery.
From windswept beaches to charming villages, Cape Cod embodies the classic American summer. Stroll through Provincetown's lively streets, sample fresh oysters and soak up the maritime heritage in every lighthouse and fishing port. Cape Cod is just as welcoming in autumn, with quiet beaches and colorful fall foliage making it an ideal place to visit at this time of year.
The great outdoors awaits in New Hampshire
On the banks of the Piscataqua River that separates New Hampshire from Maine, Portsmouth is a gem! Its historic downtown is alive with independent shops, harbor front walks and buzzing restaurants. Visitors can explore living history at the Strawberry Banke Museum or take in the town's picturesque colonial architecture. The city's mix of heritage and hip culture makes it one of New England's most inviting small cities. I will forever remember my morning stroll through the city, imaging life there in early colonial times. If you have a free evening here, Jumping Jay's Fish Café is well worth a trip, as too is Earth Eagle Brewings.
For those craving alpine scenery, head to the White Mountains. A great base is the Omni Mount Washington, with its striking position in Bretton Woods. Mount Washington is an area great for hiking, wildlife and breathtaking views, while the region is renowned for fall foliage - as scenic drives, particularly on the iconic Kancamagus Highway, light up in fiery reds and oranges.
Just sat on the veranda early in the morning, watching the sun rise from behind the mountains was a pleasant way to start the day. Two must-dos in the area are the Mount Washington Cog Railway and the Conway Scenic Railroad.
The Mount Washington Cog Railway is a historic marvel, known as the world's first mountain-climbing cog railway and a symbol of innovation in New Hampshire's White Mountains. Conceived by inventor Sylvester Marsh in the mid-19th century, it uses a remarkable rack-and-pinion system. You experience steep ascents - up to 37% - and sweeping views, all while riding vintage steam locomotives that celebrate more than 150 years of continuous operation.
The Conway Scenic Railroad offers visitors a different kind of nostalgic journey through New Hampshire's scenic valleys and villages. Traveling on restored heritage trains, you are treated to classic rail excursions departing from North Conway, winding along picturesque routes such as Crawford Notch aboard vintage carriages and through authentic historic stations,
Kennebunkport: A quaint coastal town
This picturesque town on the Maine coast is rich in maritime history and charm. Originally a shipbuilding and fishing village, it has evolved into a beloved summer destination known for its scenic beaches, historic sea captain's mansions and the bustling Dock Square filled with boutique shops, art galleries, and excellent seafood restaurants.
The town also holds historical significance as the longstanding summer retreat of the Bush family at Walker's Point. Visitors can explore landmarks like the Seashore Trolley Museum - the oldest and largest electric railway museum in the world - and the White Columns House Museum, which offers a glimpse into Kennebunkport's affluent Victorian past. With its blend of history, culture, and coastal beauty, Kennebunkport offers a quintessential New England experience.
The gardens of the Nonantum Resort, one of the properties our tours stop at, are an incredible place to watch boats and birds pass by the little lighthouse.
Portland, Maine: The foodie capital of the Northeast
Portland has risen to fame as a top food city in the USA. Its Old Port district is lined with award-winning restaurants, breweries, and bakeries. Coastal walks, working lighthouses, and the fresh salty air set the mood for Maine hospitality. Don't miss sampling local lobster and indulging in handmade ice cream.
Scales restaurant gets a five-star review from me, along with Teringua which was featured on one of my favorite Netflix shows, Somebody Feed Phil. There are countless breweries to savor and sample local brews, including Oxbow and Newscapes, which are close by in East Bayside.
Arcadia & Bar Harbor: Where land meets sea
It felt like we were driving to the end of America. Bar Harbor provides the perfect base for exploring Acadia National Park, offering endless outdoor opportunities.
Sunrise from Cadillac Mountain is world-famous and the town itself has charming boutique shops and classic seafood shacks. Nature lovers and photographers will find plenty to be inspired by. Visiting the Bar Harbor Inn, one of the destination properties on our tours, was an amazing experience. Soaking up the views over the Bay Island and Frenchman Bay was a great way to finish the trip and create memories I will keep forever.
Experience New England in the Fall
Enjoy the stunning colors of New England's golden season on one of our popular tours, taking in the incredible destinations featured above.
