{"id":232379,"date":"2021-06-17T09:00:43","date_gmt":"2021-06-17T13:00:43","guid":{"rendered":"https:\/\/www.nomadicmatt.com\/?p=232379"},"modified":"2025-08-20T17:20:39","modified_gmt":"2025-08-20T21:20:39","slug":"new-england-road-trip-itinerary","status":"publish","type":"post","link":"https:\/\/www.nomadicmatt.com\/travel-blogs\/new-england-road-trip-itinerary\/","title":{"rendered":"Road-Tripping New England: My Suggested Itinerary"},"content":{"rendered":"
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I\u2019ve said it before and I\u2019ll say it again: The United States is made for road trips<\/a>. I\u2019ve road-tripped the USA five times, spending a cumulative two years exploring its cities, towns, and parks. To me, a road trip is the best way to explore the US.<\/p>\n One region in particular that I love to drive around is New England. <\/p>\n Having grown up in Boston<\/a>, I\u2019ve spent a lot of my life in this part of the country. And yeah, I\u2019m biased because I grew up here, but I really do think New England is one of the most special areas of the country. It offers delicious seafood, friendly and welcoming people, incredible natural beauty, charm, and plenty of history.<\/p>\n If you’re thinking of visiting, here\u2019s a suggested road trip around New England to help you get a feel for the region:<\/p>\n These are some of my favorite things to do in Boston:<\/p>\n For more suggestions on what to do in the city (and there\u2019s plenty), check out my free guide to Boston<\/a>.<\/p>\n Where to Stay<\/strong>: HI Boston<\/a> – This is my favorite hostel in the city. It\u2019s clean, spacious, and social, and the staff are super friendly and helpful.<\/p>\n For more suggestions, here is my list of the best places to stay in Boston<\/a>. While you\u2019re in Portland, be sure to check out some of the city\u2019s best restaurants, including Duckfat (get the fries), Eventide Oyster Co. (best oysters in the city), and Bite into Maine (best lobster roll in the city). For drinks, head to Rising Tide Brewery.<\/p>\n Where to Stay<\/strong>: Black Elephant Hostel<\/a> – This hostel has a cool, colorful interior and social atmosphere, and is perfectly located near lots of restaurants and shopping. Moreover, on the way up from Portland, take Route 1 and stop for food along the way in any one of the numerous historic fishing towns. If you like oysters, stop at Glidden Point Oyster Farm.<\/p>\n Here are some things to see and do in and near Bar Harbor:<\/p>\n Like the rest of Maine, Bar Harbor has some wonderful places to eat. My favorites were the Travelin Lobster (best lobster roll in the area), Havana (upscale dining), and Rosalie\u2019s (delicious food all around).<\/p>\n Where to Stay<\/strong>: Bar Harbor Manor<\/a> – This is a cozy hotel right outside Acadia National Park with lots of outdoor space to relax in, free Wi-Fi, and an indoor parlor with a fireplace. Where to Stay<\/strong>: Bangor is a small town, so you\u2019ll want to compare prices on Booking.com<\/a> to see what best suits your budget. Spend a couple of days here relaxing away from the crowds, hiking the plethora of trails, spotting moose, or taking part in all the lake activities on offer. For dinner or drinks, head to the Stress Free Moose Pub in Greenville. Some of the best day hikes up the mountain are Tuckerman Ravine Trail (4.2 miles, strenuous), Lion\u2019s Head Trail (4.2 miles, strenuous), and Jewell Trail (5.2 miles, moderate).<\/p>\n Where to Stay<\/strong>: You can stay in nearby Gorham or Littleton. Check Booking.com<\/a> to see what best suits your budget. Some of my favorite things to do here are the following: <\/p>\n Where to Stay<\/strong>: There are no hostels here, so compare prices on Booking.com<\/a> to see what best suits your budget. Highlights include Thundering Falls (a 140-foot waterfall), the Long Trail (a 272-mile hike and the oldest long-distance trail in the country), and the panoramic view from the 4,000-foot Camel Hump summit.<\/p>\n Since it\u2019s a national forest, camping here is free (unless signs advise otherwise). Here are some things to see and do:<\/p>\n Where to Stay<\/strong>: There are no hostels here, so compare prices on Booking.com<\/a> to see what best suits your budget. Be sure to tour the Emily Dickinson Museum, which commemorates the poet (she was born in Amherst in 1830). The house where she was born and grew up, now converted into a museum, includes artwork, artifacts, clothing, and poetry from Dickinson\u2019s life. There are often events and poetry readings here, so check the website to see what\u2019s on during your visit. Guided tours last 60 minutes and cost $16 USD. <\/p>\n As for food, Antonio\u2019s Pizza is a must (they have some really inventive toppings). I ate a lot of it during college! I\u2019m also a big fan of Black Sheep for sandwiches and House of Teriyaki for Japanese food.<\/p>\n Where to Stay<\/strong>: There are no hostels here, so compare prices on Booking.com<\/a> to see what best suits your budget. It\u2019s just a short two-hour drive back to Boston, so feel free to stop along the way to stretch your legs. There are plenty of places to stop along the way or just do more things in Boston! Here are some things to see and do during your stay:<\/p>\n New England is one of the most beautiful parts of the United States. Its size makes it perfect for road trips, offering a nice mix of cities, small towns, and stunning natural beauty. It also has some of the best seafood in the country, lots of hiking and biking opportunities, and some of the friendliest people in the country. I\u2019m proud to have grown up in this region and encourage you to explore my backyard!<\/p>\n Need a car for your trip? Use the widget below to find the best deals with Discover Cars<\/a><\/strong>:
\n <\/p>\nDays 1-3: Boston, MA<\/h3>\n

\nKick things off in Boston, whose old colonial buildings testify to its historic roots. I grew up in this city and, even with all my world travels, it remains one of my favorites. Though it’s one of the biggest cities in America, it has more of a “large-town” feel to it rather than that of a bustling metropolis. Here, you\u2019ll find friendly locals, die-hard sports fans, lively bars, world-class restaurants, and a ton of American history to keep you busy.<\/p>\n\n
\n <\/p>\nDays 4-5: Portland, ME<\/h3>\n

\nLocated two hours from Boston, Portland, Maine, is your next stop. Due to its robust brewery scene, a historic downtown, lots of great seafood, and nearby coastal parks and lighthouses, I\u2019m a huge fan of the city. I really got to explore it on my latest trip for the first time since college and it’s just a great place to spend a couple of days. Some must-see things to do: <\/p>\n\n
\n <\/p>\nDays 6-8: Bar Harbor, ME<\/h3>\n

\nJust three hours north of Portland, Bar Harbor is the largest town near Acadia National Park, whose pristine stretch of 50,000 acres is home to Cadillac Mountain, the highest peak on the Atlantic coast. While the town itself has a population of just over 5,000 people, Bar Harbor sees a massive influx of people every summer. Be sure to plan ahead and hit the park early while you\u2019re here. <\/p>\n\n
\n <\/p>\nDay 9: Bangor, ME<\/h3>\n

\nBangor is just one hour away from Bar Harbor. Just 32,000 people call Bangor home, but it\u2019s a cute little town worth a night. There are a bunch of parks and breweries in town, and you can see Stephen King\u2019s house (he lives in Bangor). My favorite places to eat are Fiddleheads (delicious food all around) and Judy\u2019s (best diner breakfast). For a drink, head to Mason\u2019s Brewing.<\/p>\n
\n <\/p>\nDays 10-12: Moosehead Lake, ME<\/h3>\n

\nMoosehead Lake is just 2.5 hours north of Bangor. It\u2019s the second-largest lake in New England and the largest in the state. Spanning over 75,000 acres, it\u2019s perfect for fishing, boating, hiking, and relaxing. You can rent a boat or jet-ski, camp, or stay at one of the lodges. <\/p>\n
\n <\/p>\nDays 13-14: Mount Washington, NH<\/h3>\n

\nMount Washington is just over four hours southwest of Greenville. It\u2019s in the Presidential Range of the White Mountains and is the highest peak in the Northeast. While you can hike to the top if you\u2019re experienced (it\u2019s known as the most dangerous small mountain in the world), you can also take a train to the summit, where there is an observation building. <\/p>\n
\n <\/p>\nDays 15-17: Burlington, VT<\/h3>\n

\nLocated in northwest Vermont, around four hours from Mount Washington, Burlington is the largest city in the state. With just 42,000 people, it feels more like a small town than a major city. And, sitting on the shores of Lake Champlain, Burlington has a lot for outdoor enthusiasts, so try to come when the weather is nice! <\/p>\n\n
\n <\/p>\nDays 18-19: Green Mountain National Forest, VT<\/h3>\n

\nSpanning almost 400,000 acres, the Green Mountain National Forest is a gorgeous landscape home to all kinds of wildlife, including bears, moose, coyotes, beavers, deer, and more. Established in 1932, it\u2019s a beautiful place for a day hike or multiday trip (parts of the 2,190-mile Appalachian Trail can also be found here).<\/p>\n
\n <\/p>\nDays 20-22: The Berkshires, MA<\/h3>\n

\nTwo hours south of the Green Mountain National Forest are the Berkshires. This mountain range in western Massachusetts is dotted with small villages and charming towns. It\u2019s a popular vacation destination for hiking, skiing, and autumn drives to see the changing foliage. The region has something for everyone and is a perfect spot for anyone looking for outdoor activities or a romantic getaway. There are lots of summer and fall markets here too.<\/p>\n\n
\n <\/p>\nDay 23: Amherst, MA<\/h3>\n

\nAmherst is a vibrant college town and the hub of the Five College Consortium. In fact, I went to school at the nearby UMass campus. Spend a night here and enjoy the town\u2019s caf\u00e9s, bookstores, and restaurants.<\/p>\n
\n <\/p>\nDay 24: Back to Boston<\/h3>\n
\n <\/p>\nBonus Destination: Cape Cod, MA<\/h3>\n

\nIf you have more time, head to Cape Cod. You\u2019ll find pretty villages, picturesque lighthouses, tasty seafood spots, and endless shorelines. It\u2019s where everyone in the region goes for the summer. You could spend weeks here if you wanted! <\/p>\n\n
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