New England Fall Foliage Road Trip

Waterfall in New Hampshire's White Mountains 



Fall is a great time to go leaf peeping in New England. The chill has yet to set in, the colors of the changing foliage are breathtaking, plus it’s pumpkin time--we went the first part of October-- pumpkins everywhere!

This itinerary is for a nine-day trip flying directly into Boston from San Francisco, then renting a car. We drove a clockwise loop over the course of 8 days visiting all six New England states: Massachusetts, Rhode Island, Connecticut, Vermont, New Hampshire and Maine.

TIP: Pick up maps at your AAA office. Ask for the states by name, the young man helping me thought New England was part of the UK!

Pack layers for warm to cool weather. Pack good walking shoes, of course, and something light for rain.


Day 1 ~ Boston

Old Corner Book Store

Depart San Francisco. Flight is approximately 5 hours and 45 minutes. Arrive in Boston! Remember to set your clock ahead 3 hours. Rent your car and spring for the portable GPS if you haven’t brought your own. The signage back east is not as merciful as here in California. Check in to your Boston hotel. We went budget staying 2 nights at Best Western Roundhouse Suites. Ditch the car and take Boston Old Town Trolley Tour to get your bearings on the city (100 minutes $34 pp hop-on, hop-off); or use subway to get around. Their underground is efficient, economical and clean.

Day 2 ~ Boston

Union Oyster House

Walk the Freedom Trail starting at Boston Common, the oldest park in America. Pick up the guidebook at the TI for juicy historical tidbits.This 2 ½ mile walk with 16 significant historic sites. Explore Faneuil Hall Marketplace, walking on cobblestone streets with lots of shops, restaurants and historic buildings. Also Old North Church (where Paul Revere signaled of the British troops heading to Lexington). Stop at the Union Oyster House claiming to be the oldest restaurant in America (1826). Back to the hotel to clean up for a night on the town. Maybe dinner at Cuchi Cuchi, we caught a Red Sox game--it's easy to get tickets at the stadium, but be ready to haggle!





Day 3 ~ Plymouth and Cape Cod

Check out of hotel. Drive to south toward Cape Cod on Hyw 3. Drive through Quincy, past the Adams Mansion and the birthplaces of two American presidents. Drive to Plymouth (Hwy 3A--38 miles/45 minutes from Boston) Visit the Plymouth Plantation where costumed interpreters portray early 17th-century lifestyle and Mayflower II($28 for combo ticket or you can take a gander at the exterior for free) Photo stop at Plymouth Rock.

Venture on south on 3 after crossing the Cape Cod Canal you’ll now be on Hyw 6, you can visit and tour the Dexter Grist Mill and the historic Hoxie House. Then drive to Hyannis Port, and visit the memorial to President John F. Kennedy . If you have time you can possibly get in a harbor cruise, or do a little kayaking. Tip: The main highway on Cape Cod is straight down the middle of the cape with trees on each side so you will not get ocean views, or much of any views, if you opt to drive to Provincetown. There are some decent restaurants there, but it’s very out of the way if you’re not staying on the cape.

Options: tour the Kennedy Museum. We drove on to Fall River and stayed at Comfort Inn and Suites to save some bucks and get a jump on the next days driving. Tip: Eat dinner in Cape Cod!

Mystic Harbor

Day 4 ~ Rhode Island and Connecticut.

Breakfast and check out. Head into Rhode Island on 24. Drive to Newport (25 miles/40 minutes) to tour the mansions along Bellevue Avenue, and walk on Cliff Walk.

Tour Mystic, Connecticut (50mi/1 hr from Newport). Consider steamboat cruise along the Mystic River if time allows. Enjoy the coast!(54 mi/ 1 hr from Mystic). We lodged at Touch of Ireland B&B in New Haven, very friendly inn with great dinner suggestions and a lovely breakfast.

Day 5 ~ Vermont



   Mark Twain's House                                    Covered Bridge ~ Woodstock

Breakfast and check out. Before heading north, check out Yale University in New Haven. We were there on a Sunday and walked into a fun gospel church service! Travel on and stop at Hartford (34 mi) to tour Mark Twain's House and Museum. Enjoy the fall color up hwy 91 to Woodstock, Vermont (129 miles). Stopping to gather leaves to make a Fall Foliage collage of your drive through the Berkshire Mountains in Massachusetts, the Green Mountains in Vermont, the picturesque town of Woodstock. We stayed at Canterbury House B&B in Woodstock, small rooms but great old house and great location within walking of everything in town, and very fun communal breakfast.                                                               

Day 6 ~ New Hampshire

Old Red Inn

Breakfast and check out. Head to the White Mountains of New Hampshire, but first stop at beautiful Quechee Gorge and state park  Have your camera ready for the picturesque covered bridges, quaint towns, and forests and of course the fall foliage. North Conway, New Hampshire (140 miles/ 2hrs. 50 min.) Lodge at Old Red Inn in North Conway, this budget place is a little funky but in a good way! Ask for a cabin room. The breakfast was the best, very big on pumpkin decor and pumpkin breakfast items.

Tip: New Hampshire is sales tax free. There is a nice leather outlet on your way out of town and TJ Max. ~I’m just sayin’~

Day 7 ~ Maine
Drive to Portland, Maine (2 hours 65mi) Stroll the cobblestone streets of Portland’s famous Old Port Exchange, lined with boutiques, coffee houses, and art galleries. Lodged at Chadwick Inn B & B in Portland, modern inn with large rooms and a nice common room, great dinner suggestions and a made to order breakfast.

Day 8 ~ Concord


Minute Man Park            Orchard House

Breakfast and check out. Head to Boston stopping at Kennebunkport – picturesque summer retreat of many artists and writers. Drive to Concord Tour Orchard House (where Louisa May Alcott lived and wrote), visit Sleepy Hollow Cemetery and take a peak at Emerson’s family tombstones, see his house too, called The Old Manse. Retrace history in Minute Man National Park and stroll over the North Bridge where the Revolutionary War began. Explore Concord and Lexington and be sure to eat dinner in one of the quaint taverns. Lodge at Best Western Roundhouse Suites in Boston if trying to go budget.

Day 9 ~ Boston/SF

Breakfast. Shop around downtown and eat lunch if time allows. Give yourselves an hour to drive to airport and return car (26 mi./40 min) and depart for SF . This was a 6 hour 55 minute flight for us. Remember to set your watches ahead again!