52 days in Massachusetts & Vermont Itinerary

52 days in Massachusetts & Vermont Itinerary

Created using Inspirock United States trip itinerary planner

Plan created by another user. Make it yours

Route & dates

1
Provincetown
— 5 nights
2
Boston
— 6 nights
3
Concord
— 2 nights
4
South Deerfield
— 3 nights
5
Stowe
— 5 nights
6
Woodstock
— 3 nights
7
Edgartown, Martha's Vineyard
— 1 night
8
Nantucket
— 5 nights
9
Falmouth
— 2 nights
10
Plymouth
— 3 nights
11
Cambridge
— 3 nights
12
Wellfleet
— 3 nights
13
Salem
— 3 nights
14
North Adams
— 3 nights
15
Manchester
— 3 nights

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.
Step off the beaten path and head to Spas and Long Point. Give yourself a bit of retail therapy at Cortile Gallery and Atlantic Spice Company. Next up on the itinerary: stroll through Race Point Beach, appreciate the history behind Pilgrim Monument & Provincetown Museum, visit a coastal fixture at Wood End Lighthouse, and take a leisurely stroll along MacMillan Wharf.

For ratings, other places to visit, where to stay, and other tourist information, refer to the Provincetown road trip planning website.

London, UK to Provincetown is an approximately 11.5-hour flight. Due to the time zone difference, you'll gain 5 hours traveling from London to Provincetown. In February, Provincetown is little chillier than London - with highs of 3°C and lows of -3°C. Wrap up your sightseeing on the 6th (Thu) to allow time to ride a ferry to Boston.

Things to do in Provincetown

Parks · Outdoors · Museums

Side Trips

Highland Light, Atlantic Spice Company
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.
You'll explore and learn at Boston Children's Museum and The Patriots Hall of Fame. Discover out-of-the-way places like TD Garden and Currier Museum of Art. Explore the numerous day-trip ideas around Boston: Mansfield Public Library (in Mansfield), World's End (in Hingham) and National Shrine of our Lady of La Salette (in Attleboro). There's still lots to do: stop by Back Bay, admire the striking features of Marriott's Custom House, browse the exhibits of The Mapparium, and pause for some serene contemplation at King's Chapel.

To see where to stay and more tourist information, read our Boston holiday builder site.

Getting from Provincetown to Boston by ferry takes about 2.5 hours. Other options: fly; or drive. In February in Boston, expect temperatures between 4°C during the day and -5°C at night. Finish up your sightseeing early on the 12th (Wed) so you can go by car to Concord.

Things to do in Boston

Museums · Parks · Childrens Museums

Side Trips

Manchester, Mansfield Public Library, Blue Hills Reservation, Adams National Historical Park, World's End
Highlights from your plan
Boston Children's Museum ©
Boston Children's Museum
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): contemplate the long history of Louisa May Alcott's Orchard House, contemplate the long history of The Old Manse, get engrossed in the history at The Robbins House, then snap pictures at Minuteman National Park - Old North Bridge, and finally shop like a local with Harvard Alpaca Ranch. Get ready for a full day of sightseeing on the next day: steep yourself in history at Ralph Waldo Emerson House, steep yourself in history at Munroe Tavern, and then steep yourself in history at Thoreau House.

To see where to stay, photos, more things to do, and more tourist information, go to the Concord trip planner.

Traveling by car from Boston to Concord takes an hour. Alternatively, you can take a train; or take a bus. Traveling from Boston in February, Concord is slightly colder at night with lows of -9°C. Finish your sightseeing early on the 14th (Fri) to allow enough time to drive to South Deerfield.

Things to do in Concord

Historic Sites · Museums · Parks

Side Trips

Munroe Tavern, Harvard Alpaca Ranch
Highlights from your plan
Louisa May Alcott's Orchard House ©
Louisa May Alcott's Orchard House
Minuteman National Park - Old North Bridge ©
Ralph Waldo Emerson House ©
Ralph Waldo Emerson House

3
nights
South Deerfield

South Deerfield ©
South Deerfield is a census-designated place (CDP) in Deerfield, Franklin County, Massachusetts, United States. Discover out-of-the-way places like Yankee Candle Flagship Store and Chesterfield Gorge. Appreciate the collections at Frary House and Shelburne Falls Trolley Museum. Take a break from South Deerfield with a short trip to Bearsden Conservation Area in Athol, about 54 minutes away. There's lots more to do: look for all kinds of wild species at Bullitt Reservation, get engrossed in the history at Memorial Hall Museum, and experience rural life at Clarkdale Fruit Farms.

To find traveler tips, more things to do, other places to visit, and other tourist information, refer to the South Deerfield trip planning website.

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. Finish your sightseeing early on the 17th (Mon) to allow enough time to travel to Stowe.

Things to do in South Deerfield

Museums · Parks · Wildlife

Side Trips

Deerfield, Bullitt Reservation, Chesterfield Gorge, Bearsden Conservation Area, Shelburne Falls Trolley Museum
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.
Bring the kids along to Jay Peak Resort and Bolton Valley Resort. Do your shopping at Laughing Moon Chocolates and West Branch Gallery & Sculpture Park. Venture out of the city with trips to Sugarbush Resort (in Warren), Stone Corral Brewery (in Richmond) and Burlington (Battery Park & Queen City Brewery). There's lots more to do: fly down the slopes at Trapp Family Lodge Outdoor Center, sample the fine beverages at Stowe Cider, take your sightseeing to a higher altitude at Spruce Peak at Stowe, and sample the tasty concoctions at The Alchemist.

To see more things to do, other places to visit, and more tourist information, you can read our Stowe tour itinerary app.

Drive from South Deerfield to Stowe in 3 hours. In February, Stowe is little chillier than South Deerfield - with highs of -1°C and lows of -15°C. Wrap up your sightseeing on the 22nd (Sat) to allow time to drive to Woodstock.

Things to do in Stowe

Parks · Outdoors · Winter Sports

Side Trips

Burlington, Bolton Valley Resort, Sugarbush Resort, Stone Corral Brewery, Jay Peak Resort
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. Step off the beaten path and head to Killington Resort and New England Falconry. Family-friendly places like Pico Mountain and Quechee Bridge will thrill your kids. Step out of Woodstock with an excursion to Baird Farm Vermont Maple Syrup in Chittenden--about 50 minutes away. There's much more to do: steep yourself in history at Billings Farm & Museum, delve into the lush surroundings at Mount Tom, look for gifts at FH Gillingham & Sons General Store, and contemplate the waterfront views at Ottaquechee River.

To see other places to visit, ratings, more things to do, and other tourist information, go to the Woodstock trip itinerary maker website.

You can drive from Stowe to Woodstock in 1.5 hours. Alternatively, you can do a combination of train and bus; or do a combination of train and taxi. In February, daily temperatures in Woodstock can reach 0°C, while at night they dip to -13°C. Finish your sightseeing early on the 25th (Tue) to allow enough time to travel to Edgartown.

Things to do in Woodstock

Parks · Winter Sports · Outdoors

Side Trips

Baird Farm Vermont Maple Syrup, Eshqua Bog Natural Area, Pico Mountain, Killington Resort, Quechee Bridge
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), stop by Stefanie Wolf Designs, enjoy the sand and surf at Joseph Sylvia State Beach, then look for all kinds of wild species at Cedar Tree Neck Sanctuary, and finally enjoy the sea views from Edgartown Lighthouse.

To see ratings, traveler tips, where to stay, and more tourist information, read Edgartown road trip planner.

Traveling by flight from Woodstock to Edgartown takes 4.5 hours. Alternatively, you can do a combination of car and ferry; or do a combination of bus and ferry. Traveling from Woodstock in February, expect Edgartown to be somewhat warmer, temps between 5°C and -4°C. Wrap up your sightseeing on the 26th (Wed) to allow time to travel to Nantucket.

Things to do in Edgartown

Parks · Wildlife · Beaches

Side Trips

Joseph Sylvia State Beach, Cedar Tree Neck Sanctuary
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. Eschew the tourist crowds and head to Loines Observatory and Altar Rock. Museum-lovers will appreciate Maria Mitchell Association and Nantucket Lightship Basket Museum. There's still lots to do: get to know the fascinating history of Milestone Bog, don't miss a visit to Nantucket Founders Burial Ground, pause for some serene contemplation at Nantucket United Methodist Church, and stroll through Nobadeer.

For where to stay and more tourist information, go to the Nantucket trip planner.

Traveling by combination of bus and ferry from Edgartown to Nantucket takes 2.5 hours. In February in Nantucket, expect temperatures between 5°C during the day and -2°C at night. Finish your sightseeing early on the 2nd (Mon) to allow enough time to ride a ferry to Falmouth.

Things to do in Nantucket

Historic Sites · Parks · Museums
Highlights from your plan
Greater Light ©
Greater Light
Nobadeer ©
Nobadeer
Coskata-Coatue Wildlife Refuge ©
Coskata-Coatue Wildlife Refuge

2
nights
Falmouth

Falmouth ©
Falmouth is a town in Barnstable County, Massachusetts, United States; Barnstable County is coextensive with Cape Cod. Kids will appreciate attractions like Shining Sea Bikeway and St Barnabas Memorial Church. Discover out-of-the-way places like Highfield Hall & Gardens and The Falmouth Public Library. The adventure continues: enjoy the sea views from Nobska Point Lighthouse, take in the exciting artwork at McDermott Glass Studio, examine the collection at Falmouth Museums on the Green, and engage your brain at Marine Biological Laboratory.

To find maps, ratings, more things to do, and more tourist information, you can read our Falmouth day trip site.

You can ride a ferry from Nantucket to Falmouth in 2 hours. Other options are to do a combination of ferry and taxi; or do a combination of ferry and bus. In March, daily temperatures in Falmouth can reach 7°C, while at night they dip to -3°C. Wrap up your sightseeing on the 4th (Wed) to allow time to drive to Plymouth.

Things to do in Falmouth

Parks · Museums · Historic Sites

Side Trip

McDermott Glass Studio
Highlights from your plan
Highfield Hall & Gardens ©
Highfield Hall & Gardens
Nobska Point Lighthouse ©
Nobska Point Lighthouse
St Barnabas Memorial Church ©
St Barnabas Memorial Church

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.
Start off your visit on the 5th (Thu): stop by Titcomb's Bookshop, view the masterpieces at Richard Sparrow House, take an in-depth tour of Pilgrim Hall Museum, then learn about winemaking at Plymouth Bay Winery, and finally appreciate the history behind Plymouth Rock. Get ready for a full day of sightseeing on the next day: steep yourself in history at Jabez Howland House, tee off at Pinehills Golf Club, and then enjoy the sea views from Scituate Lighthouse.

To find more things to do, photos, reviews, and more tourist information, you can read our Plymouth trip maker.

Traveling by car from Falmouth to Plymouth takes an hour. Alternatively, you can do a combination of bus and taxi; or take a bus. In March, daytime highs in Plymouth are 7°C, while nighttime lows are -3°C. Wrap up your sightseeing by early afternoon on the 7th (Sat) to allow enough time to 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.
You'll discover tucked-away gems like The Harvard Museum of Natural History and MIT Museum. You'll visit kid-friendly attractions like Mount Auburn Cemetery and Memorial Drive. Step out of Cambridge to go to Fiskdale and see St. Anne's Shrine, which is approximately 1h 5 min away. There's still lots to do: take in the architecture and design of Harvard University, stop by World's Only Curious George Store, sample the tasty concoctions at Lord Hobo Brewing Company, and take a stroll through Central Square.

To see reviews, maps, more things to do, and other tourist information, use the Cambridge trip itinerary website.

Getting from Plymouth to Cambridge by car takes about an hour. Other options: do a combination of bus and subway; or do a combination of train and subway. In March, daytime highs in Cambridge are 7°C, while nighttime lows are -1°C. Finish your sightseeing early on the 10th (Tue) to allow enough 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 ©
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): enjoy the sand and surf at Mayo Beach, trek along Great Island Trail, then look for gifts at Pilgrim's Landing, and finally shop like a local with Addison Art Gallery. Get ready for a full day of sightseeing on the next day: take in the views from Uncle Tim's Bridge, then take in the exciting artwork at Left Bank Art Gallery, then get engrossed in the history at Wellfleet Historical Society & Museum, and finally steep yourself in history at Chatham's Godfrey Windmill.

To find maps, more things to do, reviews, and tourist information, read Wellfleet trip planning site.

Traveling by car from Cambridge to Wellfleet takes 2.5 hours. Alternatively, you can do a combination of bus and ferry; or do a combination of subway 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 ©
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.
Do some cultural sightseeing at Pickering Wharf and Salem Toy Museum. Family-friendly places like Parker River National Wildlife Refuge and Phillips House will thrill your kids. Step out of Salem with an excursion to Stoneface Brewing in Newington--about 1 hour away. And it doesn't end there: get engrossed in the history at Salem Witch Museum, have some family-friendly fun at Witch Pix, look for gifts at The Coven's Cottage, and admire the striking features of Gedney House.

For more things to do, where to stay, reviews, and tourist information, you can read our Salem planning site.

You can drive from Wellfleet to Salem in 2.5 hours. Alternatively, you can do a combination of bus, ferry, and train; or take a bus. In March, plan for daily highs up to 6°C, and evening lows to -3°C. Finish your sightseeing early on the 16th (Mon) so you can travel to North Adams.

Things to do in Salem

Historic Sites · Museums · Parks

Side Trips

Parker River National Wildlife Refuge, Stoneface Brewing
Highlights from your plan
The House of the Seven Gables ©
The House of the Seven Gables
Parker River National Wildlife Refuge ©
Parker River National Wildlife Refuge
Salem Maritime National Historic Site ©
Salem Maritime National Historic Site

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): grab your bike and head to Village Bike Rentals, see the interesting displays at Crane Museum of Papermaking, and then take a peaceful walk through Savoy Mountain State Forest. Here are some ideas for day two: get a taste of the local shopping with Ozzie's Glass Gallery, then steep yourself in history at Steepletop, and then sample the tasty concoctions at Bright Ideas Brewing.

For more things to do, ratings, and more tourist information, refer to the North Adams holiday planning site.

Traveling by car from Salem to North Adams takes 3 hours. In March, daily temperatures in North Adams can reach 5°C, while at night they dip to -6°C. On the 19th (Thu), wrap the sightseeing up by early afternoon so you can drive to Manchester.

Things to do in North Adams

Museums · Parks · Breweries & Distilleries

Side Trips

Steepletop, Village Bike Rentals, Ozzie's Glass Gallery, Crane Museum of Papermaking, Savoy Mountain State Forest
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 in touch with nature at Equinox Preservation Trust and Magic Mountain. Your cultural itinerary includes sights like DaVallia Gallery & Boutique and Saratoga Monument. You'll find plenty of places to visit near Manchester: Jamaica State Park (in Jamaica) and Grafton Trails & Outdoor Center (in Grafton). It doesn't end there: shop like a local with Southern Vermont Arts Center and experience rural life at North Meadow Farm.

Discover how to plan a Manchester trip in just a few steps with Inspirock's itinerary builder.

You can drive from North Adams to Manchester in 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

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

Similar plans

60 days in Massachusetts BY A USER FROM UNITED STATES February, popular sights Preferences: February Attraction style: Popular sights Pace: Medium 4 days in Vermont BY A USER FROM UNITED STATES January, popular sights Preferences: January Attraction style: Popular sights Pace: Medium 1 day in Massachusetts BY A USER FROM UNITED STATES January, popular sights Preferences: January Attraction style: Popular sights Pace: Medium 29 days in Massachusetts BY A USER FROM UNITED STATES January, popular sights Preferences: January Attraction style: Popular sights Pace: Medium 2 days in Vermont BY A USER FROM UNITED STATES January, popular sights Preferences: January Attraction style: Popular sights Pace: Medium 3 days in Vermont BY A USER FROM UNITED STATES February, popular sights Preferences: February Attraction style: Popular sights Pace: Medium 1 day in Vermont BY A USER FROM UNITED STATES May, popular sights Preferences: May Attraction style: Popular sights Pace: Medium 35 days in Massachusetts BY A USER FROM UNITED STATES December, popular sights Preferences: December Attraction style: Popular sights Pace: Medium 10 days in Massachusetts BY A USER FROM UNITED STATES June, popular sights Preferences: June Attraction style: Popular sights Pace: Medium 9 days in Massachusetts BY A USER FROM UNITED STATES January, popular sights Preferences: January Attraction style: Popular sights Pace: Medium 6 days in Vermont BY A USER FROM CANADA December, popular sights Preferences: December Attraction style: Popular sights Pace: Medium 1 day in Massachusetts BY A USER FROM UNITED STATES December, popular sights Preferences: December Attraction style: Popular sights Pace: Medium
See more plans