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Autumnal views of New England in the Fall

14 October 2025

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 an autumnal trip or a summer holiday, destinations like Boston, Portland, Cape Cod and Bar Harbor promise unforgettable memories - each with their own local flavour and unique attractions.

Great Rail journeys has 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 flavours 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 cracking food. A must is Mike's Pastry, well worth the queues to sample an enormous cannolo.

Boston's waterfront is pulsing with activity, and neighbourhoods like Back Bay overflow with shopping and dining for every taste.

The great outdoors awaits in New Hampshire

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 wildlife and breathtaking views, while the region is renowned for autumn 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 musts 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 alpine 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. Travelling 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.

Portland, Maine: The foodie capital of the northeast

Portland has risen to fame as a top food city in America. 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 favourite Netflix shows, Somebody Feed Phil. There are countless breweries to savour and sample local brews, including Oxbow and Newscapes, which are close by in East Bayside.

Experience New England in the Fall

Enjoy the glorious hues of New England's golden season on a popular tour, taking in the destinations featured above.

Spend two nights uncovering the history of Boston before sailing to mystical Salem. Head into the stunning White Mountains to ride the iconic heritage railways and drive along the Kancamagus Highway. After a boat trip across Lake Winnipesaukee, continue to the Maine coast and enjoy three nights in gastronomic Portland.

Discover New England in the Fall here.