14 days in Massachusetts Itinerary

14 days in Massachusetts Itinerary

Created using Inspirock Massachusetts tour planner

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Route & dates

14 days in Massachusetts Itinerary

Start: Norfolk
Fly:  5​h 15​min
1
Edgartown, Martha's Vineyard
— 1 night
Drive:  2​h 30​min
2
Nantucket
— 2 nights
Drive:  2​h 45​min
3
Chatham
— 2 nights
Drive:  2​h
4
Boston
— 4 nights
Drive:  2​h 30​min
5
Lenox
— 4 nights
Bus + Fly:  6​h 45​min
End: Norfolk

1
night
Edgartown, Martha's Vineyard

Edgartown ©
Edgartown is a town located on Martha's Vineyard in Dukes County, Massachusetts, United States. On the 20th (Sun), take in nature's colorful creations at Mytoi and then visit a coastal fixture at Edgartown Lighthouse.

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

Norfolk to Edgartown is an approximately 5.5-hour flight. You can also do a combination of car and ferry; or do a combination of train and ferry. Traveling from Norfolk in October, things will get slightly colder in Edgartown: highs are around 65°F and lows about 46°F. Cap off your sightseeing on the 21st (Mon) early enough to go by car to Nantucket.

Things to do in Edgartown

Historic Sites Parks Neighborhoods

Side Trips

Aquinnah, Oak Bluffs, Granary Gallery
Highlights from your plan
Edgartown Lighthouse ©
Edgartown Lighthouse
Gay Head Lighthouse ©
Gay Head Lighthouse
Granary Gallery ©
Granary Gallery

2
nights
Nantucket

Nantucket ©
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Start off your visit on the 22nd (Tue): visit a coastal fixture at Brant Point Lighthouse, then enjoy the sea views from Sankaty Head Lighthouse, and then visit a coastal fixture at Great Point Light. On the next day, appreciate the extensive heritage of Milestone Bog, see the interesting displays at Egan Maritime's Nantucket Shipwreck & Lifesaving Museum, and then learn about winemaking at Cisco Brewers.

To find ratings, reviews, maps, and more tourist information, read Nantucket trip itinerary tool .

You can drive from Edgartown to Nantucket in 2.5 hours. October in Nantucket sees daily highs of 64°F and lows of 51°F at night. Finish your sightseeing early on the 23rd (Wed) to allow enough time to drive to Chatham.

Things to do in Nantucket

Historic Sites Breweries & Distilleries Wineries
Highlights from your plan
Brant Point Lighthouse ©
Brant Point Lighthouse
Sankaty Head Lighthouse ©
Sankaty Head Lighthouse
Great Point Light ©
Great Point Light

2
nights
Chatham

Chatham ©
Chatham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. Start off your visit on the 24th (Thu): get to know the fascinating history of Fort Hill Rural Historic District, then enjoy the sea views from Highland Light, and then appreciate the extensive heritage of Wellfleet Bay Wildlife Sanctuary. Get ready for a full day of sightseeing on the next day: get engrossed in the history at Chatham Marconi Maritime Center, get engrossed in the history at Salt Pond Visitor Center, then enjoy the sea views from Nauset Lighthouse, and finally steep yourself in history at Captain Penniman House.

To find where to stay, reviews, traveler tips, and more tourist information, you can read our Chatham driving holiday planning tool .

Traveling by car from Nantucket to Chatham takes 3 hours. In October, plan for daily highs up to 63°F, and evening lows to 50°F. Wrap up your sightseeing on the 25th (Fri) early enough to drive to Boston.

Things to do in Chatham

Historic Sites Museums Parks

Side Trips

Eastham, Wellfleet Bay Wildlife Sanctuary, Highland Light
Highlights from your plan
Fort Hill Rural Historic District ©
Fort Hill Rural Historic District
Chatham Marconi Maritime Center ©
Chatham Marconi Maritime Center
Wellfleet Bay Wildlife Sanctuary ©
Wellfleet Bay Wildlife Sanctuary

4
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 of Fine Arts and New Bedford Whaling Museum will appeal to museum buffs. Visit Lizzie Borden House and National Monument to the Forefathers for their historical value. Venture out of the city with trips to Nobska Point Lighthouse (in Woods Hole), Battleship Cove (in Fall River) and Sandwich (Sandwich Glass Museum, Hoxie House, & more). There's lots more to do: get to know the fascinating history of Freedom Trail, steep yourself in history at Plymouth Rock, and explore the galleries of Old State House.

To find ratings, where to stay, and other tourist information, use the Boston attractions planner.

You can drive from Chatham to Boston in 2 hours. Another option is to take a bus. Expect a daytime high around 64°F in October, and nighttime lows around 50°F. Wrap up your sightseeing on the 29th (Tue) early enough to drive to Lenox.

Things to do in Boston

Museums Historic Sites Childrens Museums

Side Trips

Sandwich, Fall River, Plymouth, New Bedford Whaling Museum, Nobska Point Lighthouse
Highlights from your plan
Old State House ©
Old State House
Lizzie Borden House ©
Lizzie Borden House
New Bedford Whaling Museum ©
New Bedford Whaling Museum

4
nights
Lenox

Lenox ©
Lenox is an affluent town in Berkshire County, Massachusetts, United States. Explore hidden gems such as MASS MoCA and Historic Deerfield. Get a sense of the local culture at The Mount, Edith Wharton's Home and Williams College Museum of Art. Explore the numerous day-trip ideas around Lenox: Dr. Seuss National Memorial Sculpture Garden (in Springfield), Mount Greylock State Reservation (in Lanesboro) and Yankee Candle Flagship Store (in South Deerfield). There's still lots to do: take in the spiritual surroundings of National Shrine of the Divine Mercy, steep yourself in history at Hancock Shaker Village, take in the exciting artwork at Ozzie's Glass Gallery, and do a tasting at Balderdash Cellars.

To see maps, photos, reviews, and more tourist information, read Lenox online trip maker .

You can drive from Boston to Lenox in 2.5 hours. Other options are to take a bus; or take a train. Traveling from Boston in October, you can expect nighttime temperatures to be slightly colder in Lenox, with lows of 40°F. Cap off your sightseeing on the 2nd (Sat) early enough to travel back home.

Things to do in Lenox

Museums Historic Sites Parks

Side Trips

Pittsfield, Dr. Seuss National Memorial Sculpture Garden, Historic Deerfield, Ozzie's Glass Gallery, MASS MoCA
Highlights from your plan
MASS MoCA ©
MASS MoCA
The Mount, Edith Wharton's Home ©
The Mount, Edith Wharton's Home
Hancock Shaker Village ©
Hancock Shaker Village

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