52 days in Massachusetts & Vermont Itinerary

52 days in Massachusetts & Vermont Itinerary

Created using Inspirock United States trip itinerary planner

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Route & dates

52 days in Massachusetts & Vermont Itinerary

Start: London
Fly:  10​h 30​min
1
Provincetown
— 5 nights
Ferry:  1​h 30​min
2
Boston
— 6 nights
Train:  45​min
3
Concord
— 2 nights
Drive:  1​h 30​min
4
South Deerfield
— 3 nights
Drive:  3​h
5
Stowe
— 5 nights
Drive:  1​h 30​min
6
Woodstock
— 3 nights
Fly:  4​h 30​min
7
Edgartown, Martha's Vineyard
— 1 night
Drive:  2​h 30​min
8
Nantucket
— 5 nights
Drive:  3​h
9
Falmouth
— 2 nights
Drive:  45​min
10
Plymouth
— 3 nights
Drive:  1​h
11
Cambridge
— 3 nights
Drive:  2​h 15​min
12
Wellfleet
— 3 nights
Drive:  2​h 30​min
13
Salem
— 3 nights
Drive:  3​h
14
North Adams
— 3 nights
Drive:  1​h
15
Manchester
— 3 nights
Drive + Fly:  18​h 30​min
End: London

5
nights
Provincetown

Provincetown ©
A small resort town with a year-round population of just 3,000, Provincetown draws nearly 60,000 annual visitors with its scenic beaches, art colonies, galleries, theaters, and shops.
Your inner history buff will appreciate Highland Light and Wood End Lighthouse. Provincetown Art Association and Museum and Provincetown Town Hall are good opportunities to explore the local culture. There's much more to do: identify plant and animal life at Beech Forest, Provincetown, tour the pleasant surroundings at Long Point, visit a coastal fixture at Race Point Lighthouse, and kick back and relax at Race Point Beach.

For traveler tips, photos, other places to visit, and more tourist information, you can read our Provincetown day trip tool .

London, UK to Provincetown is an approximately 10.5-hour flight. You can also do a combination of flight and ferry; or do a combination of flight and bus. Traveling from London to Provincetown, you'll gain 5 hours due to the time zone difference. Expect a bit cooler temperatures when traveling from London in February; daily highs in Provincetown reach 3°C and lows reach -3°C. Cap off your sightseeing on the 6th (Thu) early enough to catch the ferry to Boston.

Things to do in Provincetown

Parks Outdoors Museums

Side Trips

Atlantic Spice Company, Highland Light
Highlights from your plan
Beech Forest, Provincetown ©
Beech Forest, Provincetown
Cape Cod Provincelands Trail ©
Cape Cod Provincelands Trail
Long Point ©
Long Point

6
nights
Boston

Boston ©
Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Museum-lovers will appreciate Boston Children's Museum and The Patriots Hall of Fame. Step out of the city life by going to World's End and Nantasket Beach. Change things up with these side-trips from Boston: Manchester (SEE Science Center & Currier Museum of Art), Mansfield Public Library (in Mansfield) and National Shrine of our Lady of La Salette (in Attleboro). The adventure continues: visit Back Bay, look for all kinds of wild species at Blue Hills Reservation, get into the urban bustle at TD Garden, and admire the striking features of Marriott's Custom House.

To see ratings, where to stay, and tourist information, read Boston vacation maker website .

Traveling by ferry from Provincetown to Boston takes 1.5 hours. Alternatively, you can fly; or drive. In February, daytime highs in Boston are 4°C, while nighttime lows are -5°C. Cap off your sightseeing on the 12th (Wed) early enough to catch the train to Concord.

Things to do in Boston

Museums Parks Childrens Museums

Side Trips

Manchester, The Patriots Hall of Fame, National Shrine of our Lady of La Salette, Mansfield Public Library, World's End
Highlights from your plan
Back Bay ©
Back Bay
Adams National Historical Park ©
Adams National Historical Park
World's End ©
World's End

2
nights
Concord

Concord ©
Concord is a town in Middlesex County, Massachusetts, in the United States. Kick off your visit on the 13th (Thu): take an in-depth tour of Louisa May Alcott's Orchard House, steep yourself in history at The Old Manse, get engrossed in the history at The Robbins House, then take in the views from North Bridge, and finally wander the wide-open spaces of Harvard Alpaca Ranch. Get ready for a full day of sightseeing on the next day: steep yourself in history at Ralph Waldo Emerson House, then steep yourself in history at Munroe Tavern, and then contemplate the long history of Thoreau House.

Plan my trip to Concord with suggested itineraries provided by Inspirock.

You can take a train from Boston to Concord in an hour. Alternatively, you can drive; or take a bus. Expect a bit cooler evenings in Concord when traveling from Boston in February, with lows around -9°C. Wrap up your sightseeing on the 14th (Fri) early enough to drive to South Deerfield.

Things to do in Concord

Historic Sites Museums Parks

Side Trips

Harvard Alpaca Ranch, Munroe Tavern
Highlights from your plan
Louisa May Alcott's Orchard House ©
Louisa May Alcott's Orchard House
North Bridge ©
North Bridge
Munroe Tavern ©
Munroe Tavern

3
nights
South Deerfield

South Deerfield ©
South Deerfield is a census-designated place (CDP) in Deerfield, Franklin County, Massachusetts, United States. Eschew the tourist crowds and head to Yankee Candle Flagship Store and Frary House. Wells-Thorn House and Shelburne Falls Trolley Museum are good opportunities to explore the local culture. Explore South Deerfield's surroundings by going to Chesterfield Gorge (in Chesterfield) and Bearsden Conservation Area (in Athol). The adventure continues: identify plant and animal life at Bullitt Reservation, relax in the rural setting at Clarkdale Fruit Farms, and get engrossed in the history at Memorial Hall Museum.

For ratings, traveler tips, more things to do, and other tourist information, go to the South Deerfield journey maker site .

You can drive from Concord to South Deerfield in 1.5 hours. In February, daytime highs in South Deerfield are 1°C, while nighttime lows are -11°C. Wrap up your sightseeing on the 17th (Mon) early enough to travel to Stowe.

Things to do in South Deerfield

Museums Parks Historic Sites

Side Trips

Deerfield, Chesterfield Gorge, Shelburne Falls Trolley Museum, Bullitt Reservation, Bearsden Conservation Area
Highlights from your plan
Yankee Candle Flagship Store ©
Yankee Candle Flagship Store
Frary House ©
Frary House
Memorial Hall Museum ©
Memorial Hall Museum

5
nights
Stowe

Stowe ©
Stowe bustles in winter when skiers and snowboarders flock here to challenge themselves on the long, steep trails careening down Vermont's tallest peak, Mt.
Get in touch with nature at Trapp Family Lodge Outdoor Center and Gentle Giants Sleigh and Carriage Rides. Attractions like Jay Peak Resort and Bolton Valley Resort make great kid-friendly stops. Get out of town with these interesting Stowe side-trips: Sugarbush Resort (in Warren), Burlington (Battery Park & Queen City Brewery) and Stone Corral Brewery (in Richmond). There's much more to do: stroll through Stowe Mountain, take in the exciting artwork at West Branch Gallery & Sculpture Park, sample the fine beverages at Green Mountain Distillers, and sample the tasty concoctions at Stowe Cider.

To find out how to plan a trip to Stowe, use our trip itinerary maker.

Traveling by car from South Deerfield to Stowe takes 3 hours. Plan for slightly colder temperatures traveling from South Deerfield in February, with highs in Stowe at -1°C and lows at -15°C. Finish your sightseeing early on the 22nd (Sat) so you can drive to Woodstock.

Things to do in Stowe

Parks Outdoors Winter Sports

Side Trips

Burlington, Bolton Valley Resort, Jay Peak Resort, Green Mountain Distillers, Stone Corral Brewery
Highlights from your plan
Trapp Family Lodge Outdoor Center ©
Trapp Family Lodge Outdoor Center
Sugarbush Resort ©
Sugarbush Resort
Jay Peak Resort ©
Jay Peak Resort

3
nights
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. Popular historic sites such as Billings Farm & Museum and FH Gillingham & Sons General Store are in your itinerary. Explore hidden gems such as Killington Resort and Pico Mountain. Take a break from Woodstock with a short trip to Baird Farm Vermont Maple Syrup in Chittenden, about 50 minutes away. Next up on the itinerary: take in the awesome beauty at Mount Tom, identify plant and animal life at New England Falconry, take in the views from Taftsville Covered Bridge, and explore the activities along Ottaquechee River.

For maps, reviews, other places to visit, and other tourist information, refer to the Woodstock day trip planning tool .

Drive from Stowe to Woodstock in 1.5 hours. Alternatively, you can do a combination of train and bus; or take a train. Expect a daytime high around 0°C in February, and nighttime lows around -13°C. Finish your sightseeing early on the 25th (Tue) so you can travel to Edgartown.

Things to do in Woodstock

Parks Nature Winter Sports

Side Trips

Pico Mountain, Killington Resort, Quechee Bridge, Eshqua Bog Natural Area, Baird Farm Vermont Maple Syrup
Highlights from your plan
Billings Farm & Museum ©
Billings Farm & Museum
Killington Resort ©
Killington Resort
Mount Tom ©
Mount Tom

1
night
Edgartown, Martha's Vineyard

Edgartown ©
Edgartown is a town located on Martha's Vineyard in Dukes County, Massachusetts, United States. On the 26th (Wed), look for gifts at Stefanie Wolf Designs, then kick back and relax at Joseph Sylvia State Beach, then identify plant and animal life at Cedar Tree Neck Sanctuary, and finally visit a coastal fixture at Edgartown Lighthouse.

Take the guesswork out of planning a Edgartown vacation by using our trip itinerary maker.

You can fly from Woodstock to Edgartown in 4.5 hours. Alternatively, you can do a combination of car and ferry; or do a combination of bus and ferry. Expect a bit warmer temperatures when traveling from Woodstock in February; daily highs in Edgartown reach 5°C and lows reach -4°C. Wrap up your sightseeing on the 26th (Wed) early enough to drive to Nantucket.

Things to do in Edgartown

Parks Beaches Outdoors

Side Trips

Cedar Tree Neck Sanctuary, Joseph Sylvia State Beach
Highlights from your plan
Cedar Tree Neck Sanctuary ©
Cedar Tree Neck Sanctuary
Edgartown Lighthouse ©
Edgartown Lighthouse
Stefanie Wolf Designs ©
Stefanie Wolf Designs

5
nights
Nantucket

Nantucket ©
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Get some cultural insight at Milestone Bog and Loines Observatory. Escape the urban bustle at Nobadeer and Windswept Cranberry Bog. There's still lots to do: get to know the fascinating history of Altar Rock, identify plant and animal life at Coskata-Coatue Wildlife Refuge, stop by The Hub, and don't miss a visit to Nantucket Founders Burial Ground.

For ratings, photos, maps, and tourist information, read Nantucket online holiday planner .

Getting from Edgartown to Nantucket by car takes about 2.5 hours. In February, daily temperatures in Nantucket can reach 5°C, while at night they dip to -2°C. Finish your sightseeing early on the 2nd (Mon) so you can drive to Falmouth.

Things to do in Nantucket

Parks Historic Sites Museums
Highlights from your plan
Coskata-Coatue Wildlife Refuge ©
Coskata-Coatue Wildlife Refuge
Windswept Cranberry Bog ©
Windswept Cranberry Bog
Greater Light ©
Greater Light

2
nights
Falmouth

Falmouth ©
Falmouth is a town in Barnstable County, Massachusetts, United States; Barnstable County is coextensive with Cape Cod. Discover out-of-the-way places like Shining Sea Bikeway and Nobska Point Lighthouse. Appreciate the collections at Highfield Hall & Gardens and McDermott Glass Studio. Next up on the itinerary: stroll through Cornelia Carey Sanctuary (The Knob), browse the collection at The Falmouth Public Library, see the interesting displays at Falmouth Museums on the Green, and take in the spiritual surroundings of St Barnabas Memorial Church.

For maps and more tourist information, you can read our Falmouth trip itinerary builder site .

Traveling by car from Nantucket to Falmouth takes 3 hours. In March in Falmouth, expect temperatures between 7°C during the day and -3°C at night. Finish your sightseeing early on the 4th (Wed) to allow enough time to drive to Plymouth.

Things to do in Falmouth

Parks Historic Sites Museums

Side Trip

McDermott Glass Studio
Highlights from your plan
Highfield Hall & Gardens ©
Highfield Hall & Gardens
Nobska Point Lighthouse ©
Nobska Point Lighthouse
Buzzards Bay Discovery Center ©
Buzzards Bay Discovery Center

3
nights
Plymouth

Plymouth ©
Rightly calling itself "America's Hometown," Plymouth holds a prominent place in the nation's history and culture as the site of the first Puritan colony.
Kick off your visit on the 5th (Thu): stop by Titcomb's Bookshop, contemplate the long history of Richard Sparrow House, get engrossed in the history at Pilgrim Hall Museum, then learn about winemaking at Plymouth Bay Winery, and finally pause for some photo ops at Plymouth Rock. Keep things going the next day: steep yourself in history at Jabez Howland House, then play a few rounds at Pinehills Golf Club, and then enjoy the sea views from Scituate Lighthouse.

To see maps, ratings, reviews, and tourist information, go to the Plymouth trip app .

Traveling by car from Falmouth to Plymouth takes an hour. Alternatively, you can take a bus; or take a bus. In March, daytime highs in Plymouth are 7°C, while nighttime lows are -3°C. On the 7th (Sat), wrap the sightseeing up by early afternoon so you can drive to Cambridge.

Things to do in Plymouth

Historic Sites Museums Shopping

Side Trips

Scituate Lighthouse, Titcomb's Bookshop
Highlights from your plan
Jabez Howland House ©
Jabez Howland House
Pilgrim Hall Museum ©
Pilgrim Hall Museum
Scituate Lighthouse ©
Scituate Lighthouse

3
nights
Cambridge

Cambridge ©
Best known as the location of two internationally renowned universities, Cambridge sits just across the Charles River from Boston.
Visit Mount Auburn Cemetery and St. Anne's Shrine for their historical value. Get a sense of the local culture at The Harvard Museum of Natural History and Harvard University. Next up on the itinerary: get curious at MIT Museum, cruise along Memorial Drive, stop by World's Only Curious George Store, and stop by Central Square.

For maps, other places to visit, more things to do, and tourist information, you can read our Cambridge trip planner.

Traveling by car from Plymouth to Cambridge takes an hour. Alternatively, you can take a bus; or take a train. In March, plan for daily highs up to 7°C, and evening lows to -1°C. Wrap up your sightseeing on the 10th (Tue) to allow time to drive to Wellfleet.

Things to do in Cambridge

Historic Sites Museums Outdoors

Side Trips

St. Anne's Shrine, Lord Hobo Brewing Company, Cutler Park
Highlights from your plan
The Harvard Museum of Natural History ©
Mount Auburn Cemetery ©
Mount Auburn Cemetery
St. Anne's Shrine ©
St. Anne's Shrine

3
nights
Wellfleet

Wellfleet ©
Wellfleet is a town in Barnstable County, Massachusetts, United States, and is located halfway between the "tip" and "elbow" of Cape Cod. Start off your visit on the 11th (Wed): kick back and relax at Mayo Beach, trek along Great Island Trail, then look for gifts at Pilgrim's Landing, and finally take in the exciting artwork at Addison Art Gallery. Keep things going the next day: take in the views from Uncle Tim's Bridge, view the masterpieces at Left Bank Art Gallery, then get engrossed in the history at Wellfleet Historical Society Museum, and finally don't miss a visit to Chatham's Godfrey Windmill.

For other places to visit, traveler tips, maps, and other tourist information, refer to the Wellfleet trip planner .

You can drive from Cambridge to Wellfleet in 2.5 hours. Alternatively, you can take a bus; or do a combination of ferry and bus. In March, daytime highs in Wellfleet are 5°C, while nighttime lows are -1°C. On the 13th (Fri), wrap the sightseeing up by early afternoon so you can drive to Salem.

Things to do in Wellfleet

Museums Parks Outdoors

Side Trips

Chatham, Addison Art Gallery
Highlights from your plan
Left Bank Art Gallery ©
Left Bank Art Gallery
Great Island Trail ©
Great Island Trail
Wellfleet Historical Society & Museum ©

3
nights
Salem

Salem ©
Best known for its 1692 witch trials, Salem has a number of significant historical sites, a bustling downtown, and many witch-themed attractions.
Your cultural itinerary includes sights like Phillips House and Salem Witch Museum. You'll visit kid-friendly attractions like The House of the Seven Gables and Pickering Wharf. Get out of town with these interesting Salem side-trips: Parker River National Wildlife Refuge (in Newburyport) and Stoneface Brewing (in Newington). There's lots more to do: steep yourself in history at Salem Maritime National Historic Site, stop by The Coven's Cottage, contemplate in the serene atmosphere at Grace Episcopal Church, and admire the striking features of Ropes Mansion.

To see reviews, maps, where to stay, and tourist information, read Salem travel planning tool .

You can drive from Wellfleet to Salem in 2.5 hours. Alternatively, you can ride a ferry; or take a bus. March in Salem sees daily highs of 6°C and lows of -3°C at night. Wrap up your sightseeing on the 16th (Mon) to allow time to travel to North Adams.

Things to do in Salem

Historic Sites Parks Museums

Side Trips

Stoneface Brewing, Parker River National Wildlife Refuge
Highlights from your plan
The House of the Seven Gables ©
The House of the Seven Gables
Phillips House ©
Phillips House

3
nights
North Adams

North Adams ©
North Adams is a city in Berkshire County, Massachusetts, United States. Start off your visit on the 17th (Tue): tour the pleasant surroundings at Village Bike Rentals, examine the collection at Crane Museum of Papermaking, and then delve into the lush surroundings at Savoy Mountain State Forest. Get ready for a full day of sightseeing on the 18th (Wed): take in the exciting artwork at Ozzie's Glass Gallery, contemplate the long history of Steepletop, and then indulge your thirst for a good beer at Bright Ideas Brewing.

For photos, maps, and more tourist information, use the North Adams journey planning app .

Getting from Salem to North Adams by car takes about 3 hours. In March, daytime highs in North Adams are 5°C, while nighttime lows are -6°C. Wrap up your sightseeing by early afternoon on the 19th (Thu) to allow time for the car ride to Manchester.

Things to do in North Adams

Parks Museums Nature

Side Trips

Crane Museum of Papermaking, Savoy Mountain State Forest, Steepletop, Village Bike Rentals, Ozzie's Glass Gallery
Highlights from your plan
MASS MoCA ©
MASS MoCA
Crane Museum of Papermaking ©
Crane Museum of Papermaking
Village Bike Rentals ©
Village Bike Rentals

3
nights
Manchester

Manchester ©
Manchester is a town in, and one of two shire towns (county seats) of, Bennington County, Vermont, United States. Get outdoors at Equinox Preservation Trust and Jamaica State Park. You'll explore and learn at Southern Vermont Arts Center and DaVallia Art & Accents. Get out of town with these interesting Manchester side-trips: Grafton Trails & Outdoor Center (in Grafton) and Saratoga Monument (in Victory Mills). It doesn't end there: hit the slopes at Magic Mountain and experience rural life at North Meadow Farm.

For reviews, ratings, and tourist information, use the Manchester road trip website .

Getting from North Adams to Manchester by car takes about an hour. In March in Manchester, expect temperatures between 5°C during the day and -7°C at night. You will leave for home on the 22nd (Sun).

Things to do in Manchester

Parks Winter Sports Outdoors

Side Trips

Saratoga Monument, Grafton Trails & Outdoor Center, DaVallia Art & Accents, Magic Mountain, Jamaica State Park
Highlights from your plan
Jamaica State Park ©
Jamaica State Park
Equinox Preservation Trust ©
Equinox Preservation Trust
Southern Vermont Arts Center ©
Southern Vermont Arts Center

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