Massachusetts
5
Day Itinerary •
USA
Five days in Massachusetts lets you explore the full extraordinary breadth of the Bay State, from the Revolutionary heritage of Boston and the magnificent Cape Cod National Seashore to the extraordinary Berkshire Hills, the remarkable Salem witch heritage and the literary landscape of Concord and Walden Pond. This route covers the complete Massachusetts experience. The extraordinary Freedom Trail and North End of Boston, the magnificent Race Point Beach and Provincetown, the remarkable Plimoth Patuxent and Plymouth Rock, the extraordinary Salem October heritage and the magnificent Tanglewood and the Berkshires.
Best Time To Visit
April to June or September to November
Getting There
Fly into Boston Logan (BOS)
Getting Around
MBTA in Boston. Rental car for Cape Cod and Berkshires.
Budget Per Day
Approx $130 to $220 per person per day
Difficulity
Easy, mostly walking, driving and cycling
DAY 1
BOSTON
MORNING
BOSTON FREEDOM TRAIL AND THE REVOLUTIONARY HERITAGE
The Freedom Trail is the most extraordinary Revolutionary War heritage walk in America, its extraordinary 2.5-mile red-painted line connecting the Massachusetts State House, Park Street Church, the Granary Burying Ground, King's Chapel, the Old Corner Bookstore, the Old South Meeting House, the Old State House and the Boston Massacre Site. Faneuil Hall, the cradle of liberty where the Sons of Liberty met, is unmissable. All free. Drive: MBTA from airport
MIDDAY
PAUL REVERE HOUSE, OLD NORTH CHURCH AND THE NORTH END
The Paul Revere House is the oldest surviving structure in downtown Boston, its extraordinary 1680 building the home from which Revere departed on his midnight ride of April 18 1775. The Old North Church from whose steeple two lanterns signaled the British approach is the most extraordinary church in Revolutionary America. The North End's extraordinary cannoli at Mike's and Modern Pastry, the finest Italian pastry debate in America, are unmissable. Revere House entry approx $6. Drive: 15 min walk
AFTERNOON
BEACON HILL AND THE BOSTON PUBLIC GARDEN
Beacon Hill is the most extraordinary historic neighborhood in Boston, its extraordinary Federal-style brick rowhouses on Acorn Street, the finest residential street in New England, the purple-glassed windows and the remarkable Massachusetts State House with its 23-karat gold dome giving the finest 19th-century streetscape in America. The Boston Public Garden with its extraordinary swan boats and the oldest botanical garden in America, and Boston Common dating to 1634, are both free.
💎 HIDDEN GEM
The extraordinary Arnold Arboretum in Jamaica Plain is the finest hidden park in Boston, its extraordinary 281-acre living tree collection with the finest lilac display in New England each May giving the most extraordinary free botanical experience in Massachusetts. Free. 20 minutes from downtown Boston on the MBTA.
🍽 WHERE TO EAT
Breakfast: Tatte Bakery, Boston The finest breakfast in Boston. Extraordinary Israeli-inspired pastries and strong coffee. | Lunch: Neptune Oyster, North End The most celebrated oyster bar in Boston. Extraordinary New England clam chowder and lobster roll. | Dinner: No. 9 Park, Boston The finest restaurant in Boston. Extraordinary local New England produce and wine.
DAY 2
CAPE COD
MORNING
CAPE COD NATIONAL SEASHORE AND RACE POINT BEACH
The Cape Cod National Seashore protects the most extraordinary barrier beach landscape in New England, its extraordinary 40-mile Atlantic coast including Race Point Beach at the very tip of Cape Cod, the finest white sand and dune landscape in Massachusetts. The extraordinary Province Lands dune road gives the finest aerial view of the Cape's outer beach. The Highland Light is the oldest lighthouse on Cape Cod. Province Lands bike trail gives the finest cycling in the seashore. Entry $25 per vehicle. Drive: 2 hr drive
MIDDAY
PROVINCETOWN AND MACMILLAN WHARF WHALE WATCHING
Provincetown is the most extraordinary town in Massachusetts, its extraordinary Pilgrim Monument towering above the most vibrant small town in New England and the MacMillan Wharf whale watching boats offering the finest humpback whale encounter on the Atlantic coast. The Wellfleet oysters at Mac's Seafood just down the Cape give the finest raw bar experience in Massachusetts. Whale watching approx $55, monument entry approx $16. Drive: 15 min drive
AFTERNOON
CAPE COD RAIL TRAIL CYCLING AND WELLFLEET
The Cape Cod Rail Trail is the most extraordinary rail trail in New England, its extraordinary 25-mile paved path from Dennis to Wellfleet through pine barrens, cranberry bogs and kettle pond landscapes giving the finest cycling experience in Massachusetts. The extraordinary Wellfleet Bay Wildlife Sanctuary gives the finest migratory shorebird watching on the Cape. Bike hire available in Brewster and Orleans. Trail free, sanctuary entry approx $8.
💎 HIDDEN GEM
The extraordinary Great Island Trail in Wellfleet is the finest hidden coastal hike on Cape Cod, its extraordinary 8-mile loop through salt marsh, beach plum thicket and barrier spit giving the most extraordinary wild Cape Cod coastal experience entirely unknown to most visitors. Free. Best at low tide.
🍽 WHERE TO EAT
Breakfast: Cafe Heaven, Provincetown The finest breakfast in Provincetown. Extraordinary local Cape Cod ingredients. | Lunch: Mac's Seafood, Wellfleet The finest raw bar on Cape Cod. Extraordinary Wellfleet oysters and local clam chowder. | Dinner: The Mews Restaurant, Provincetown The finest restaurant in Provincetown. Extraordinary local Cape Cod seafood.
DAY 3
PLYMOUTH AND SALEM
MORNING
PLIMOTH PATUXENT AND MAYFLOWER II
Plimoth Patuxent is the most extraordinary living history museum in New England, its extraordinary recreation of the 1627 English Pilgrim village with costumed interpreters and the remarkable Wampanoag Homesite giving the finest insight into the first Thanksgiving and the founding of Plymouth Colony. The Mayflower II replica ship in Plymouth Harbor gives the finest Pilgrim maritime heritage. Plymouth Rock, America's most extraordinary disappointment, is free. Plimoth entry approx $30. Drive: 1.5 hr drive
MIDDAY
SALEM, THE MOST EXTRAORDINARY WITCH HERITAGE TOWN IN AMERICA
Salem is the most extraordinary heritage town in Massachusetts, its extraordinary 1692 witch trial history preserved in the Salem Witch Museum, the Peabody Essex Museum and the remarkable Witch Trials Memorial giving the finest dark history experience in New England. The extraordinary Charter Street Cemetery with the oldest Puritan graves in Salem and the remarkable Chestnut Street Federal architecture give the finest historic street in Massachusetts. Museum entry approx $16. Drive: 1 hr drive
AFTERNOON
SALEM HERITAGE TRAIL AND THE PEABODY ESSEX MUSEUM
The Peabody Essex Museum in Salem is the most extraordinary art and culture museum in Massachusetts outside Boston, its extraordinary collection of maritime art, Essex County decorative arts and the remarkable Yin Yu Tang, a complete 200-year-old Chinese house transported from Anhui Province to Salem, giving the finest museum experience on the North Shore. The Salem Heritage Trail gives the finest self-guided walking tour of the city. PEM entry approx $20.
💎 HIDDEN GEM
The extraordinary House of the Seven Gables in Salem is the finest hidden literary heritage site in Massachusetts, its extraordinary 1668 mansion that inspired Hawthorne's famous novel giving the most atmospheric colonial house tour in Salem. Entry approx $20.
🍽 WHERE TO EAT
Breakfast: Pilgrim Sands Hotel, Plymouth The finest breakfast in Plymouth. Extraordinary local Massachusetts produce on Plymouth Harbor. | Lunch: Sea Salt, Marblehead Outstanding North Shore lunch. Extraordinary local Massachusetts seafood with harbor views. | Dinner: Turner's Seafood, Salem The finest restaurant in Salem. Extraordinary local Massachusetts seafood.
DAY 4
CONCORD AND LEXINGTON
MORNING
WALDEN POND AND THOREAU'S CABIN SITE
Walden Pond is the most extraordinary literary heritage site in Massachusetts, the glacial kettle pond where Henry David Thoreau built his cabin and lived from 1845 to 1847, writing Walden, the most extraordinary work of American environmental literature. The cairn at the original cabin site, the replica cabin at the Thoreau Farm and the extraordinary swimming in Walden Pond itself give the most extraordinary literary pilgrimage in America. Entry $8 per vehicle. Drive: 1.5 hr drive
MIDDAY
MINUTE MAN NATIONAL HISTORICAL PARK, LEXINGTON TO CONCORD
Minute Man National Historical Park is the most extraordinary Revolutionary War landscape in America, its extraordinary 2.5-mile Battle Road from the Lexington Green where the first shots were fired to Concord's North Bridge where the Redcoats were turned back giving the finest Revolutionary War walk in the country. The extraordinary North Bridge with Daniel Chester French's Minute Man statue and the Old Manse of Emerson and Hawthorne are unmissable. Entry free. Drive: 10 min drive
AFTERNOON
CONCORD'S LITERARY HERITAGE, SLEEPY HOLLOW CEMETERY
Concord is the most extraordinary literary town in America, its extraordinary Authors Ridge in Sleepy Hollow Cemetery where Thoreau, Emerson, Hawthorne and Louisa May Alcott are buried together in the finest literary resting place in the world. The Orchard House, home of the Alcott family where Louisa May Alcott wrote Little Women, and the remarkable Emerson House give the finest 19th-century American literary heritage experience. Orchard House entry approx $12.
💎 HIDDEN GEM
The extraordinary Great Meadows National Wildlife Refuge in Concord is the finest hidden birdwatching site in Massachusetts, its extraordinary freshwater marsh along the Concord River giving the finest migratory waterfowl experience in eastern Massachusetts. Free. Adjacent to the Minute Man battlefield.
🍽 WHERE TO EAT
Breakfast: Concord's Colonial Inn The finest breakfast in Concord. Extraordinary local Massachusetts produce in America's most literary inn. | Lunch: Main Streets Market and Cafe, Concord Outstanding local Concord lunch. Extraordinary Massachusetts produce near Walden Pond. | Dinner: 80 Thoreau, Concord The finest restaurant in Concord. Extraordinary local Massachusetts farm-to-table cuisine.
DAY 5
THE BERKSHIRES
MORNING
MASS MOCA, THE LARGEST CONTEMPORARY ART MUSEUM IN THE UNITED STATES
MASS MoCA in North Adams is the most extraordinary contemporary art museum in America, its extraordinary 250,000-square-foot complex of 19th-century mill buildings converted to 26 galleries giving the finest single-site contemporary art experience in the United States. The extraordinary James Turrell retrospective, the Sol LeWitt wall drawings and the remarkable Gunnar Schonbeck collection of sound instruments give the finest contemporary art experience in New England. Entry approx $20. Drive: 2.5 hr drive
MIDDAY
TANGLEWOOD MUSIC FESTIVAL AND THE BERKSHIRE HILLS
Tanglewood in Lenox is the most extraordinary outdoor music venue in America, the summer home of the Boston Symphony Orchestra where lawn tickets give the finest classical music experience in New England under the Berkshire Hills sky. The extraordinary Stockbridge Village of Norman Rockwell, the remarkable Chesterwood studio of sculptor Daniel Chester French and the fine Berkshire Botanical Garden give the finest cultural landscape in western Massachusetts. Lawn tickets from approx $22. Drive: 30 min drive
AFTERNOON
STOCKBRIDGE AND THE NORMAN ROCKWELL MUSEUM
The Norman Rockwell Museum in Stockbridge is the most extraordinary illustrative art museum in America, its extraordinary collection of 998 original Rockwell paintings and drawings including the Four Freedoms series giving the finest American illustrative art experience in the country. The extraordinary Stockbridge Main Street, unchanged since Rockwell painted his famous 1967 Christmas scene, and the remarkable Red Lion Inn since 1773 give the finest New England village experience. Museum entry approx $25.
💎 HIDDEN GEM
The extraordinary Bash Bish Falls in Mount Washington State Forest is the finest hidden waterfall in Massachusetts, its extraordinary 80-foot cascade in the Taconic Mountains near the New York border giving the most extraordinary waterfall hike in the Berkshires on a 0.7-mile trail. Free. The most extraordinary hidden gem in western Massachusetts.
🍽 WHERE TO EAT
Breakfast: Public, North Adams The finest breakfast near MASS MoCA. Extraordinary local Berkshires produce and strong coffee. | Lunch: Nudel, Lenox The finest restaurant in Lenox. Extraordinary local Berkshires ingredients in a tiny extraordinary space. | Dinner: Red Lion Inn, Stockbridge The most legendary dinner in the Berkshires since 1773. Extraordinary local Massachusetts produce.
Where To Stay
Boston and Provincetown, Nights 1 to 2 Liberty Hotel or Brass Key Guesthouse. Approx $160 to $320. Salem and Concord, Nights 3 to 4 Hawthorne Hotel or Colonial Inn. Approx $140 to $260 per night. Lenox, Night 5 Blantyre or Cranwell Resort. Approx $180 to $500 per night.
Top Tips
1. Salem in October is the finest Halloween in America. Book accommodation 6 months ahead minimum.
2. Tanglewood lawn tickets give the finest summer classical music experience in America. Bring a picnic.
3. MASS MoCA in North Adams is the largest contemporary art museum in the US. Allow a full day.
4. Cape Cod Rail Trail cycling from Dennis to Wellfleet is the finest rail trail in New England. Bike hire easy.
5. Walden Pond: arrive early on summer weekends. The lot fills by 9am and the gate closes at capacity.
6. Boston North End cannoli: buy from Modern Pastry on a weekday to avoid the weekend Mike's Pastry queue.
Total Budget
$130 to $220/day