12 days in New England, Maine & Vermont Itinerary
Created using Inspirock United States trip builder
Start: Philadelphia
Drive
1
Newport
— 1 night
Drive
2
Boston
— 2 nights
Drive
3
Portland
— 2 nights
Drive
4
Wolfeboro
— 2 nights
Drive
5
Jamaica
— 2 nights
Drive
6
Manchester
— 2 nights
Drive
End: Philadelphia
Mon, Apr 3 - Fri, Apr 14
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Newport — 1 night

City by the Sea
Start off your visit on the 3rd (Mon): tour the pleasant surroundings at Newport Butterfly Zoo, then appreciate the extensive heritage of Cliff Walk, and then appreciate the extensive heritage of Ocean Drive Historic District.
Plan trip to Newport with our itinerary maker to find out where to go and what to do.
Philadelphia to Newport is an approximately 4.5-hour car ride. You can also do a combination of flight and car; or drive; or do a combination of train and bus. In April, Newport is little chillier than Philadelphia - with highs of 54°F and lows of 39°F. On the 4th (Tue), you'll travel to Boston.
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Plan trip to Newport with our itinerary maker to find out where to go and what to do.
Philadelphia to Newport is an approximately 4.5-hour car ride. You can also do a combination of flight and car; or drive; or do a combination of train and bus. In April, Newport is little chillier than Philadelphia - with highs of 54°F and lows of 39°F. On the 4th (Tue), you'll travel to Boston.
Side Trip
Highlights from your trip
Boston — 2 nights

Beantown
Kick off your visit on the 4th (Tue): get engrossed in the history at John F. Kennedy Presidential Museum & Library and then appreciate the extensive heritage of Freedom Trail. Get ready for a full day of sightseeing on the 5th (Wed): steep yourself in history at Granary Burying Ground, admire the masterpieces at Museum of Fine Arts, and then stroll around Boston Public Garden.
To see traveler tips, more things to do, where to stay, and tourist information, use the Boston tour itinerary app.
Traveling by car from Newport to Boston takes 2 hours. Alternatively, you can drive; or take a bus; or do a combination of bus and train. In April, plan for daily highs up to 56°F, and evening lows to 40°F. On the 6th (Thu), you'll travel to Portland.
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To see traveler tips, more things to do, where to stay, and tourist information, use the Boston tour itinerary app.
Traveling by car from Newport to Boston takes 2 hours. Alternatively, you can drive; or take a bus; or do a combination of bus and train. In April, plan for daily highs up to 56°F, and evening lows to 40°F. On the 6th (Thu), you'll travel to Portland.
Highlights from your trip
Portland — 2 nights
The Forest City
Kick off your visit on the 6th (Thu): cast your line with a fishing tour and then grab your bike and head to Eastern Promenade Trail. On the 7th (Fri), you'll have a packed day of sightseeing: admire the masterpieces at Portland Museum of Art, then take an in-depth tour of Victoria Mansion, and then indulge your taste buds at Food & Drink.
To find ratings, traveler tips, photos, and other tourist information, read our Portland trip builder tool.
Getting from Boston to Portland by car takes about 2 hours. Other options: drive; or take a bus; or take a train. Traveling from Boston in April, you can expect nighttime temperatures to be little chillier in Portland, with lows of 34°F. Finish your sightseeing early on the 8th (Sat) so you can drive to Wolfeboro.
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To find ratings, traveler tips, photos, and other tourist information, read our Portland trip builder tool.
Getting from Boston to Portland by car takes about 2 hours. Other options: drive; or take a bus; or take a train. Traveling from Boston in April, you can expect nighttime temperatures to be little chillier in Portland, with lows of 34°F. Finish your sightseeing early on the 8th (Sat) so you can drive to Wolfeboro.
Side Trips
Highlights from your trip
Wolfeboro — 2 nights

To find other places to visit, maps, ratings, and more tourist information, read Wolfeboro trip planner.
You can drive from Portland to Wolfeboro in 2 hours. In April, daytime highs in Wolfeboro are 53°F, while nighttime lows are 33°F. Finish your sightseeing early on the 10th (Mon) so you can travel to Jamaica.
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You can drive from Portland to Wolfeboro in 2 hours. In April, daytime highs in Wolfeboro are 53°F, while nighttime lows are 33°F. Finish your sightseeing early on the 10th (Mon) so you can travel to Jamaica.
Highlights from your trip
Jamaica — 2 nights

Kick off your visit on the 10th (Mon): tour the pleasant surroundings at Stratton Mountain. On the 11th (Tue), you'll have a packed day of sightseeing: stop by Vermont Country Store, stroll through Magic Mountain, and then get a dose of the wild on Husky Works Mushing Co..
For traveler tips, more things to do, ratings, and more tourist information, refer to the Jamaica road trip planner.
Explore your travel options from Wolfeboro to Jamaica with the Route module. April in Jamaica sees daily highs of 55°F and lows of 31°F at night. Cap off your sightseeing on the 12th (Wed) early enough to travel to Manchester.
more
For traveler tips, more things to do, ratings, and more tourist information, refer to the Jamaica road trip planner.
Explore your travel options from Wolfeboro to Jamaica with the Route module. April in Jamaica sees daily highs of 55°F and lows of 31°F at night. Cap off your sightseeing on the 12th (Wed) early enough to travel to Manchester.
Side Trips
Highlights from your trip
Manchester — 2 nights
On the 12th (Wed), explore the different monuments and memorials at Elm Grove Cemetery, then contemplate the long history of Olde Mistick Village, and then immerse yourself in nature at Gillette Castle State Park. Here are some ideas for day two: hike along MDC Reservoir #6, contemplate the long history of The Mark Twain House & Museum, and then take in the awesome beauty at Case Mountain.
To find out how to plan a trip to Manchester, use our trip itinerary maker.
Use the Route module to find suitable travel options from Jamaica to Manchester. Traveling from Jamaica in April, plan for somewhat warmer nights in Manchester, with lows around 39°F. Cap off your sightseeing on the 14th (Fri) early enough to go by car back home.
more
To find out how to plan a trip to Manchester, use our trip itinerary maker.
Use the Route module to find suitable travel options from Jamaica to Manchester. Traveling from Jamaica in April, plan for somewhat warmer nights in Manchester, with lows around 39°F. Cap off your sightseeing on the 14th (Fri) early enough to go by car back home.
Side Trips
Highlights from your trip
Maine travel guide
The Pine Tree State
The easternmost state in New England, Maine features an indented coastline and forested interior, carved eons ago by receding glaciers. Maine includes more lighthouses and quaint resort villages than you could ever hope to explore in a single trip, but the state is also one of the country's most sparsely populated, the majority of its land pristine and uninhabited wilderness. The temperate coastal regions, historically supported by fishing and lobstering, contain most of the state's urban centers and are the most popular spots in the state for holidays. The sea is the focus here, so it shouldn't come as a surprise that water plays an important role in the distinct character of the state, shaping its economy, tourism, cuisine, politics, sports, and art.
Vermont travel guide
The Green Mountain State
Known for its autumn foliage and maple syrup, Vermont is one of the country's smallest states in terms of both population and geographic area. Despite its small size and mostly rural character, the state boasts many picturesque places to visit, including Lake Champlain, one of the nation's largest freshwater bodies. Split in half by the Green Mountains--a popular holiday destination for hiking and skiing--Vermont features a rolling landscape dotted with farms and quaint towns known for their family-run inns, antique shops, and restaurants. Be sure to explore the state's many wild areas while on vacation, but beware of the so-called "mud season," a period of a few weeks when the state's unpaved roads become undrivable due to spring thaw.
Connecticut travel guide
The Constitution State
Perhaps best known for its renowned private and public universities, Connecticut was once home to the country's first law school and still boasts one of the oldest secondary schools in America. More than just a small state packed with students, Connecticut offers visitors a chance to explore some of New England's finest tourist attractions while on vacation, including lighthouses, beaches, theaters, museums, galleries, and restaurants. Despite its small size, the state also boasts two large casino complexes, both located on Native American reservations. Rich in history and natural beauty, Connecticut draws newcomers from around the world, with large Polish, Chinese, and Hispanic communities.