30 days in Massachusetts, Rhode Island & Connecticut Itinerary

30 days in Massachusetts, Rhode Island & Connecticut Itinerary

Created using Inspirock United States trip itinerary planner

Plan created by another user. Make it yours

Route & dates

1
Boston
— 6 nights
2
Provincetown
— 5 nights
3
New Shoreham, Block Island
— 3 nights
4
Newport
— 5 nights
5
Mystic
— 4 nights
6
Hartford
— 6 nights

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.
Explore the numerous day-trip ideas around Boston: Sandwich (Old King's Hwy, Heritage Museums & Gardens, &more), The House of the Seven Gables (in Salem) and Plymouth (Plimoth Plantation, The Jenney, &more). There's lots more to do: walk around Boston Public Garden, appreciate the extensive heritage of Freedom Trail, explore the world behind art at Museum of Fine Arts, and get lost in a book at John F. Kennedy Presidential Museum & Library.

Quickly create a custom-made itinerary for Boston using our trip planner.

New York City to Boston is an approximately 3.5-hour flight. You can also drive; or take a train. Expect little chillier temperatures when traveling from New York City in September; daily highs in Boston reach 75°F and lows reach 59°F. Finish your sightseeing early on the 7th (Mon) so you can ride a ferry to Provincetown.

Things to do in Boston

Museums · Parks · Historic Sites

Side Trips

Sandwich, Plymouth, The House of the Seven Gables, Dolphin & Whale Watching
Highlights from your plan
Boston Public Garden ©
Boston Public Garden
Museum of Fine Arts ©
Museum of Fine Arts
Freedom Trail ©
Freedom Trail

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.
You'll find plenty of places to visit near Provincetown: Eastham (Captain Penniman House, Salt Pond Visitor Center, &more) and Orleans (Church of the Transfiguration & Nauset Beach). Next up on the itinerary: browse the exhibits of Pilgrim Monument & Provincetown Museum, kick back and relax at Cape Cod National Seashore, tour the pleasant surroundings at Marconi Beach, and admire the masterpieces at Provincetown Art Association and Museum.

To find where to stay, maps, other places to visit, and more tourist information, read Provincetown day trip planning app.

You can ride a ferry from Boston to Provincetown in 2.5 hours. Other options are to fly; or drive. In September, plan for daily highs up to 71°F, and evening lows to 57°F. Finish your sightseeing early on the 12th (Sat) to allow enough time to travel to New Shoreham.

Things to do in Provincetown

Outdoors · Beaches · Parks

Side Trips

Eastham, Orleans, Corn Hill Beach, Cape Cod National Seashore, Marconi Beach
Highlights from your plan
Cape Cod National Seashore ©
Cape Cod National Seashore
Pilgrim Monument & Provincetown Museum ©
Pilgrim Monument & Provincetown Museum
Salt Pond Visitor Center ©
Salt Pond Visitor Center

3
nights
New Shoreham, Block Island

New Shoreham ©
New Shoreham is a town in Washington County, Rhode Island, United States. New Shoreham is known for nature, historic sites, and beaches. Your plan includes some of its best attractions: take in the dramatic natural features at Mohegan Bluffs, view the masterpieces at Jessie Edwards Studio, enjoy the sea views from South East Lighthouse, and take in the waterfront at Mansion Beach.

To find traveler tips, reviews, photos, and tourist information, use the New Shoreham itinerary maker.

Getting from Provincetown to New Shoreham by combination of flight and ferry takes about 7 hours. Other options: do a combination of ferry, train, and bus; or do a combination of bus and ferry. In September, plan for daily highs up to 71°F, and evening lows to 61°F. Wrap up your sightseeing on the 15th (Tue) early enough to travel to Newport.

Things to do in New Shoreham

Parks · Outdoors · Trails

Side Trip

Abrams Animal Farm
Highlights from your plan
Mohegan Bluffs ©
Mohegan Bluffs
South East Lighthouse ©
South East Lighthouse
Jessie Edwards Studio ©
Jessie Edwards Studio

5
nights
Newport

Newport ©
With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Change things up with these side-trips from Newport: Chatham Marconi Maritime Center (in North Chatham), John F Kennedy Hyannis Museum (in Hyannis) and Chatham Lighthouse Beach (in Chatham). Next up on the itinerary: examine the collection at The Breakers, appreciate the extensive heritage of Cliff Walk, tour the old-fashioned way with a train tour, and get a tailor-made plan with Newport Helicopter Tours.

For more things to do, other places to visit, photos, and other tourist information, read our Newport itinerary planner.

Getting from New Shoreham to Newport by combination of ferry and taxi takes about 2.5 hours. Other options: ride a ferry. In September, daytime highs in Newport are 74°F, while nighttime lows are 58°F. Finish your sightseeing early on the 20th (Sun) so you can drive to Mystic.

Things to do in Newport

Outdoors · Historic Sites · Parks

Side Trips

Falmouth, Chatham, John F Kennedy Hyannis Museum
Highlights from your plan
The Breakers ©
The Breakers
Cliff Walk ©
Cliff Walk
Boat Tours & Water Sports

4
nights
Mystic

Mystic ©
A historical leading seaport, Mystic has maintained a strong respect for the past.
Get out of town with these interesting Mystic side-trips: Skydive Danielson (in Killingly) and Main Street Park, Essex Village (in Essex). Next up on the itinerary: see the interesting displays at Mystic Seaport Museum, try your luck at Foxwoods Resort Casino, steep yourself in history at Olde Mistick Village, and take a tour of Charles W. Morgan.

For reviews, traveler tips, other places to visit, and tourist information, you can read our Mystic trip planner.

Drive from Newport to Mystic in 1.5 hours. Alternatively, you can do a combination of bus and train. Expect a daytime high around 75°F in September, and nighttime lows around 58°F. Cap off your sightseeing on the 24th (Thu) early enough to go by car to Hartford.

Things to do in Mystic

Outdoors · Tours · Adventure

Side Trips

Foxwoods Resort Casino, The Submarine Force Museum, Skydive Danielson, Main Street Park, Essex Village, Mystic Whaler Cruises
Highlights from your plan
Skydive Danielson ©
Skydive Danielson
Mystic Seaport Museum ©
Mystic Seaport Museum
Mystic Whaler Cruises ©
Mystic Whaler Cruises

6
nights
Hartford

Hartford ©
Hartford is the capital of the U.S. Venture out of the city with trips to Lime Rock Park (in Lakeville), Winsted (Soldiers' Monument and Memorial Park & Winchester Historical Society) and Norman Rockwell Museum (in Stockbridge). There's lots more to do: stroll around Stanley park, admire the masterpieces at Hill-Stead Museum, stroll through Ashuwillticook Rail Trail, and steep yourself in history at The Mark Twain House & Museum.

For traveler tips, where to stay, more things to do, and more tourist information, read our Hartford online trip builder.

You can drive from Mystic to Hartford in 1.5 hours. Other options are to take a train; or do a combination of train and bus. In September in Hartford, expect temperatures between 78°F during the day and 57°F at night. Finish up your sightseeing early on the 30th (Wed) so you can go by car back home.

Things to do in Hartford

Outdoors · Museums · Adventure

Side Trips

Winsted, Wickham Park, Connecticut Fallen Firefighters Memorial, Adventure Rooms, The Clark Art Institute
Highlights from your plan
The Adventure Park at Storrs ©
The Adventure Park at Storrs
Stanley park ©
Stanley park
Norman Rockwell Museum ©
Norman Rockwell Museum

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