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Two Week New England Road Trip Itinerary: Massachusetts, Rhode Island, Connecticut
This 14-day New England road trip through Massachusetts, Rhode Island, and Connecticut is full of American history. Learn about the Revolutionary War, experience the life of the Pilgrims, the 1692 Salem Witch Trials, and the wealth of the Gilded Age. You will also visit America’s favorite beach town and have the opportunity to take a ride across Cape Cod’s sand dunes before relaxing on an island (or two). Do not miss the once-in-a-lifetime experience to be kissed by a Beluga Whale at the Mystic Aquarium!
You are excited to begin your road trip through New England and want to know the best time of year to visit, where to stay, must-see attractions, and what to eat while there. Researching the best things to do on a road trip through New England while working full time is overwhelming and you don’t have hours to spend on the internet. Save time and plan an unforgettable trip full of top activities with this ultimate New England road trip itinerary through Massachusetts, Rhode Island, and Connecticut.
Read 10 Day Road Trip Through Maine, New Hampshire, and Vermont
New England Road Trip Planner
When is the Best Time to Visit New England?
New England experiences all four seasons. The best time to visit New England for great weather and fewer crowds is in the spring (May to June) or fall (September to October). Spring temperatures range from highs in the 50s to 70s degrees F and the blooming of cherry blossoms. Summer temperatures range in the 80s, so this is a perfect time to visit the beach. However, it is the high season so book early and expect high prices. Fall temperatures from mid-September to early October are often in the 70s. Fall brings the changing of the leaves mid to late October. Winter is cold. Expect December, January, and February high temperatures of 37- 42 and low temperatures in the 20s. Snow is possible from November through April; January is typically the snowiest month of the year. The Boston Marathon, St Patrick’s Day, and Independence Day are popular times to visit Boston. Halloween is a very popular time to visit Salem and the islands and beach cities are busy during the summer months.
What is the Best Way to Travel in New England?
This New England itinerary utilizes planes, trains, buses, ferries, and a rental car. Save precious PTO by flying from your home to Boston Massachusetts. Use the Metro to explore the sights in Boston. Take a day trip to Salem Massachusetts by train, Salem is a walkable city. Then jump on a ferry from Boston to Provincetown, Provincetown is also a walkable city. You will then ride a bus to cross the Cape Cod National Seashore to catch ferries to Nantucket and Martha’s Vineyard returning to Woods Hole. In Woods Hole, you will rent a car for the remainder of the trip. Return the rental car to Boston Logan International Airport and fly home from Boston. This trip requires a lot of planning, but don’t worry, the specific of each step is described below.
How Long Do You Need to See New England?
The New England region is located in the Northeastern section of the US. It includes the states of Maine, New Hampshire, Vermont, Massachusetts, Rhode Island, and Connecticut. This itinerary is a fast-paced 14 days in Massachusetts, Rhode Island, and Connecticut. If you have more PTO, begin in Portland Maine. Spend 10 days exploring Maine, New Hampshire, and Vermont. Instead of departing in Portland, drive South and reverse the following itinerary.
Read 10 Day Road Trip Through Maine, New Hampshire, and Vermont
How Expensive is New England?
According to Budget Your Trip, the average daily budget for a New England road trip is between $200-$250 – this includes gas, a rental car, lodging, food, drink, and entry fees.
What to Pack for a New England Road Trip
New England experiences all four seasons. In the winter pack sweaters, a heavy coat, gloves, and a scarf. Expect snow; bring heavy socks and winter boots. Rain is common in the Spring, be sure to pack an umbrella and jacket. Summer is great weather to visit the beach, be sure to bring a bathing suit. Thunderstorms may occur in the summer, bring an umbrella to be prepared. Late Fall is “sweater weather” and a jacket is needed in the evening.
New England Road Trip Highlights
Boston Massachusetts | Freedom Trial | Boston Tea Party | Beacon Hill | Salem Massachusetts Witch Trials | House of Seven Gables | Cape Cod | Provincetown Massachusetts | US National Seashore | Nantucket Massachusetts | Martha’s Vineyard Massachusetts | Providence Rhode Island | Newport Rhode Island | Gilded Age Mansions | Mystic Connecticut | Mystic Aquarium | Plymouth Massachusetts | Plymouth Rock | Plimoth Plantation
Day by Day Guide for a Road Trip to New England (14 days, 13 nights)
ROUTE AT A GLANCE: Boston Massachusetts – Salem Massachusetts – Provincetown Massachusetts – Nantucket Massachusetts – Martha’s Vineyard Massachusetts – Providence Rhode Island – Newport Rhode Island – Mystic Connecticut – Plymouth Massachusetts – Boston Massachusetts
HOW MANY DAYS: 14 days
Day 1, 2, and 3: Arrive in Boston Massachusetts
Boston is an amazing city full of American history. In fact, there are 58 National Historic Landmarks and almost 300 historic sites. In addition, you will find public gardens, brownstones, brick sidewalks, gas lamps, food halls, and breweries. Spend the next two days exploring the city and eating all the amazing foods Boston is known for: Boston baked beans, Boston chowder, Boston cream pie, lobster rolls, fried clams, and apple cider donuts. Be sure to walk the Freedom Trail and visit the Boston Tea Party Museum.
Fly into Boston Logan International Airport. The Silver Line provides free bus transportation into the city, and there are marked stops directly outside of each airport terminal. Yotel is a good mid-range hotel option in the Seaport Area. The hotel is 10 steps from the courthouse stop on the Silver Line and close to attractions, restaurants, and Cisco Brewers. Be sure to enjoy a seafood dinner at the Union Oyster House, America’s oldest restaurant.
Read Things to Do in Boston Massachusetts
Day 4: Salem Massachusetts
Salem is famous for the 1692 Salem Witch Trials. Ride the Salem trolley for a city overview, follow the Salem Heritage Trail, visit the House of Seven Gables or the Mayflower ship, tour the Witch House, attend a witch trial reenactment, have your palm read, attend a séance or learn to cast spells. Start the day early, there are so many things to do in Salem it is hard to decide how to spend your one day!
Head to Boston’s North Station and take the 30 min train ride to Salem on the Newburyport/Rockport Line. Salem is a walkable city. It is a 10-minute walk on Washington Street from the Salem Train Depot to the attractions on Essex Street.
Read One Day in Salem Massachusetts
Day 5: Provincetown Massachusetts
Provincetown sits at the northernmost tip of Cape Cod on the U.S. National Seashore. The city has been called America’s favorite beach town. You will find the Pilgrim Monument, US National Seashore, sand dunes, dune shacks, lighthouses, beaches, shopping, cabaret, lobster rolls, and fried clams. Be sure to take a dune tour of the Cape Cod National Seashore and dune shacks. Provincetown Massachusetts is a fun destination, don’t miss my one-day itinerary to use your time wisely!
Check out of the Boston hotel and take the 9 am Boston Harbor Cruise direct ferry from Boston to Provincetown Massachusetts. Grab a coffee and a muffin before arriving at 66 Long Wharf early for an 8 am check-in. The ferry ride is 1.5 hours and docks at MacMillan Pier in the heart of Provincetown at 10:30 am. Be sure to photograph the Boston skyline while the ferry departs and the Long Point Light Station as approaching MacMillan Pier. Tip: Book the 11 am sand dune tour with Art’s. It is a 5-minute walk from the ferry and they will store your suitcase for you.
Read Day Trip to Provincetown Massachusetts
Day 6: Nantucket Massachusetts
Nantucket is an island in Massachusetts full of history and listed as a National Historic Landmark. Nantucket is the perfect Cape Cod Island to rejuvenate and have a little fun. You will find crushed shell walkways, cobblestoned streets, bicycles with wicker baskets, a bluff walk full of shaker homes covered in roses, tall seagrass beaches, a wharf full of yachts, Main Street boutiques, and more. You only have one day in Nantucket, plan it well!
Check out of the Provincetown hotel and take the Plymouth and Brockton bus from behind the Chamber of Commerce on the Macmillian Pier to the Hyannis Transportation Center. The bus leaves at 6:30 am and arrives at the center at 8 am. Jump on the shuttle to the HyLine Ferry to Nantucket. Arrive at the ferry at 8:45 for a 9:30 departure, and grab another cup of coffee and a snack. Arrive in Nantucket at 10:30 and check into your hotel or bed and breakfast.
Read Nantucket Day Trip Itinerary
Day 7 and 8: Martha’s Vineyard Massachusetts
Martha’s Vineyard is an island in Massachusetts best known as the filming location for the movie Jaws. This island is the perfect Cape Cod spot to relax. You will find beaches, gingerbread cottages, old Captain Homes, Alpacas, lobster ice cream, lighthouses, copper lanterns, fishing boats, and, of course, Jaws (at least the famous bridge).
Check out of the Nantucket accommodation and walk to Straight Wharf for a 9:30 arrival. Take the Hyline Ferry to Martha’s Vineyard Oak Bluffs departing at 10:30 and arriving at 11:40. Check into the hotel and head to Circuit Avenue for lunch (and lobster ice cream) before checking out the Gingerbread Houses. On the second day, purchase an all-day bus pass to visit Edgartown, the Big Bridge made famous in Jaws, and see the alpacas.
Read Martha’s Vineyard Day Trip Itinerary
Day 9: Providence Rhode Island
Providence Rhode Island is full of history and worth a quick overnight stop. You will find the country’s first indoor shopping mall, First Baptist Church, colonial houses, a canal walk, gondola rides, the Superman building, street art, and coffee milk. Be sure to attend the WaterFire Celebration.
Check out of your Martha’s Vineyard hotel and walk back to the Oak Bluffs terminal for a 7 am arrival. No reservation is required, go straight to the terminal and purchase your ticket to Woods Hole. Depart Oak Bluffs at 7:30 am and arrive in Woods Hole at 8:15. Pick up your rental car needed for the remainder of this trip from the Falmouth Steamship Terminal and drive to Providence.
Read Things to Do in Providence Rhode Island
Day 10 and 11: Newport Rhode Island
Newport Rhode Island is famous for its Gilded Age mansions and America’s Cup competition. You will find mansion tours, a gorgeous harbor full of yachts, a cliff walk, lighthouses, Easton’s Beach, Bowen’s Wharf, Bannister Wharf, Thames Street, and many sailboats. Plan to visit two mansions a day, and purchase a discounted pass from the Preservation Society here.
Read 48 Hours in Newport Rhode Island
Day 12: Mystic Connecticut
Mystic Connecticut was made famous by Julia Robert’s first major role in the movie Mystic Pizza. You will find a historic seaside town, Mystic Seaport Village living museum, the Mystic Aquarium, and Beluga Whales, movable bridges, souvenir shops, apple cider donuts, lobster rolls, and more. Consider booking a Beluga Whale experience at the Mystic Aquarium and be sure to eat a slice of Mystic pizza.
Read One Day in Mystic Connecticut
Day 13: Plymouth Massachuttes
Plymouth Massachusetts has been called America’s hometown. You will find the famous Plymouth Rock, the Mayflower, Pilgrims, cranberry bogs, lobster rolls, breweries, distilleries, and wineries. Be sure not to miss learning how the first Pilgrims lived at Plimoth Plantation living history museum.
Read Things to Do in Plymouth Massachusetts
Day 14: Return Flight from Boston Massachuttes
Return to Boston and drop the rental car off at Boston Logan International Airport. Return to the city and check into your hotel for one final night. Do last-minute sightseeing missed the first few days of the trip and stop at Faneuil Hall Marketplace for a final lobster roll or bowl of Boston Clam Chowder.
Be sure to check the Massachusetts, Rhode Island, and Connecticut Office of Tourism for upcoming festivals, special events, and what’s happening during your stay.
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