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Autumn in New England

Visit Boston, The Berkshires, Stowe, Jackson, Acadia NP, Kennebunkport, Cape Ann & Salem

Driving through New England in Autumn is a magical experience, best enjoyed in late September and October.

Red and gold leaves combine with winding roads, stunning scenery and charming New England towns. This “Autumn in New England” road trip is specifically designed to give you the best possible chance of seeing the leaves at their most glorious point. Visit gorgeous destinations like Cape CodStowe and Acadia National Park during the area’s very best time of year. So, Happy leaf-peeping!


Autumn in New England 14 nights

Remember, any and all of our pre packaged road trips can be altered to meet your exact needs and wants. Do you have more or less than 14 days for your Autumn in New England road trip? No problem, we can bolt on extra nights to allow more time to explore or shorten the number of destinations as required. Just let us know when requesting your quote.

You timed the fall colour perfectly...thank you


Boston Skyline

Day 1

Arrive for Boston, New England's foremost city

If seeing New England's foliage at its very best is your plan, then you should aim to take this road trip during late September and early October. Catching the leaves turn every shade of red and gold can be a tricky business. So, we've specifically designed this particular New England route to pass through the very best leaf-peeping areas, along varying altitudes. This will give you the best possible chance of seeing New England's autumn colour at its absolute optimum time. After touching down in New England, grab a cab and head into Boston for 3 nights and 2 days of exploring this historic city on foot.

  • Key location: Boston, MA
  • Boston, MA

Boston Common

Day 2

Walk Boston Common and The Freedom Trail

Boston Public Gardens and neighbouring Boston Common will both give you your first glimpse of New England’s fall colour as you stroll around the park’s trees. From here, you can pick up Boston’s famous Freedom Trail. This 2.5 mile history hike takes anywhere from 90 minutes to half a day to complete, depending on how many stops you make. At the end of the Trail lies the Bunker Hill Monument and the nearby USS Constitution Museum.

  • Key location: Boston, MA
  • Boston, MA

Acorn Street, Beacon Hill

Day 3

Back Bay, Beacon Hill & Boston's best bits

Boston’s remaining highlights include shopping in Back Bay, walking the cobbled streets of upscale Beacon Hill and a visit to the New England Aquarium. If timing allows, then try to take in a ball game at the home of the Red Sox - Fenway Park. Lastly, after two full days of sight-seeing, fans of the classic sitcom "Cheers" might want to swing by the original bar to say hello to Sam and the guys.

  • Key location: Boston, MA
  • Boston, MA

Off to The Berkshires

Day 4

Let your

Collect your car and head west out of town, your first drive will take you across the state to the far west of Massachusetts. Here you’ll find “The Berkshires” area, which is known for its gigantic “summer cottages”, built by wealthy Bostonians and New Yorkers looking to escape the summer heat. Today, many of these former mansions have now been converted to charming B&Bs, welcoming leaf-peepers from around the world.

  • Key location: The Berkshires, MA
  • The Berkshires, MA
  • 130 Miles

Leaf-Peeping Heaven

Day 5

A full day to discover The Berkshires towns and villages

From your base in The Berkshires, you’ll be able to explore the area’s quaint small towns like Lenox, Stockbridge and Lee to name just three. I wonder which will be your favourite? Your Road trip Pack will tell you everything you need to know to get the most from your visit.

  • Key location: The Berkshires, MA
  • The Berkshires, MA

Vermont's Back Roads

Day 6

North through the Green Mountains of Vermont

Discover more of New England’s autumn colour by heading north through the Green Mountains of Vermont on your way to Stowe. In Fall, the Green Mountains change to a spectacular mix of reds and gold. Be sure to follow the route described in your Road Trip Pack so you can enjoy the very best scenery and stopping points along the way. Once you’ve reached the pretty town of Stowe, we highly recommend a rewarding dinner at The Whip restaurant which is located on Main Street.

  • Key location: Green Mountains, VT
  • Stowe, VT
  • 180 Miles

Stowe, Vermont

Day 7

The pretty little town of Stowe, Vermont

A full day to enjoy the charms of this lovely Vermont village. Read a book by an open fire, shop for trinkets in the General Store or cruise around looking for pumpkin patches or even a fun maize maze. Feeling energetic? Then head over to Stowe's ski area on Mountain Road and take the gondola up the mountain for some epic fall colour views, before hiking back down the hill.

  • Key location: Stowe, VT
  • Stowe, VT

Kancamagus Hwy

Day 8

From the Green Mountains to the White Mountains

You’ll leave the Green Mountains of Vermont for the White Mountains of New Hampshire today. We highly recommend that you take a slight detour along the super scenic Kancamagus Highway on your way to your New Hampshire hotel. This 36 mile stretch of road is considered one of the very best places to see autumn colour in New England.

  • Key location: The White Mountains, NH
  • Jackson, NH
  • 120 Miles

Jackson's Bridges

Day 9

Discover Jackson and Mount Washington

Jackson, New Hampshire is peppered with quintessential New England “Covered Bridges”, these bridges with roofs are cleverly designed so the winter snow doesn’t damage the bridge below. Mount Washington is the highest State Park in New England, whilst Mount Washington itself dominates the area. Consider taking the Mt. Washington Auto Road for a staggering view from the 6288 ft summit.

  • Key location: Mt Washington, NH
  • Jackson, NH

Acadia National Park

Day 10

The East Coasts premier National Park

Today you’ll leave New Hampshire and enter Maine en route to the east coasts premier national park - Acadia National Park. Today’s drive is the longest on of the trip, however half the miles are on speedy (but scenic) Interstates, so it should only take around 4 to 5 hours to complete. We’ve allowed for three nights in Acadia, so take your time and be sure to explore as you go.

  • Key location: Acadia NP
  • Bar Harbor, ME
  • 220 Miles Miles

Autumn in Acadia

Day 11

Discover the beauty of Acadia National Park

People have been drawn to the rugged coast of Maine throughout history. Awed by its beauty and diversity, early 20th-century visionaries donated the land that became Acadia National Park. Today visitors come to Acadia to hike granite peaks, bike historic carriage roads, or relax and enjoy the scenery.

  • Key location: Acadia, NP
  • Bar Harbor, ME

Acadia at Dusk

Day 12

A second full day in Acadia National Park

End your time in Acadia National Park by watching the sunset from the top of Cadillac Mountain. This is the highest point on the North Atlantic seaboard, you'll be able to witness an impressive sunset over autumnal New England below.

  • Key location: Acadia, NP
  • Bar Harbour, ME

Kennebunkport, Maine

Day 13

Time to head south and explore Maine's coastline

Enjoy a hearty breakfast before heading south along Maine’s coastline to find cute Kennebunkport. Along the way, you can visit some of the New England towns which dot the Atlantic coast - These include Camden, Boothbay and the State capital Portland. Once in Kennebunkport, why not enjoy a delicious crab dinner, which this town is rightly famous for.

  • Key location: Coastal Maine
  • Kennebunkport, ME
  • 180 Miles

Salem, Massachusetts

Day 14

Last Leg - Cute Cape Ann and spooky Salem

We’ve saved one of the best days until last, Cape Ann isn’t as famous as Boston or Acadia. However, today's drive will take you through some superb New England towns and landscapes. Highlights include Crane Beach, Essex and Rockport at the tip of Cape Ann. You’ll then finish your Autumn in New England road trip with a spooky overnight stop in Salem. This lovely small town was made famous by the Witch Trials of 1692. Today, Salem’s historical past makes for an interesting last night, especially as Halloween is just around the corner. The following day, you'll complete this 900-mile leaf-peeping road trip with a short drive to Boston Airport.

  • Key location: Cape Ann, MA
  • Salem, MA
  • 70 Miles

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