Tips for a New England road trip from Boston in late September
Hey all, hopefully this kind of content is ok - if not, I'll take it to Tripadvisor. I'm from the SF Bay Area and work will be taking me to Boston the last week of September. I have always wanted to see New England, especially Maine. New England is mostly foreign to me, haven't spent much time in that part of the country at all. After I'm done with business, I was thinking of renting a car and taking a short road trip, maybe 3-4 nights, and moseying up the coast through MA, NH, and ME. Then back home through Boston. Would love to see VT but it's further away from my understanding. It's ok if I don't see everything, I just want to get a taste of autumn in New England. If colors are happening (probably too early), awesome, if they aren't it will still be cool.
Are there any must-see stops, activities, or even common road trip routes/itineraries you'd recommend? Thanks for any tips.
Life long New Englander here. I’d start by driving up I-95 to Portland, ME. On your way up there, you can stop in Portsmouth, NH and walk around the downtown area or go check out Strawberry Banke if you want to see som history stuff. After Portsmouth, you can shoot across the bridge into Kittery to do some shopping of the Kittery Trading Post and the outlets. Then make your way up to Portland where you can spend the night and check out some of the surrounding area like the Old Port or Fort William Park. From Portland, I’d recommend driving out to North Conway, NH and travel through the White Mountains. You can check out Mount Washington, see the Mount Washington Grand Hotel, the Cog Railway and more. There’s tons of awesome stuff to see in the whites and that is the place to be for foliage. I’d recommend driving down the Kancamagus highway while you’re up there as it has some amazing views. Once you make your way across to I-93, you can drive down into Franconia Notch and see where the Old Man in the Mountain used to be before he fell. You can take the tram up to the top of Cannon Mountain if you want a good view. There is also a real short easy hike nearby called Artist Bluff that has a great lookout of the notch. From there, you can make your way back down I-93, stopping in Meredith, NH to check out Lake Winnipesaukee and the surrounding area. After that, if you are into military history, then I recommend the NH Veteran’s Cemetery. It is one of the nicest and well kept veteran cemeteries in the country that isn’t Arlington. After that, you can make your way back down to Boston.
This is a lot to do in 3-4 days and you could easily spend 3-4 days alone in each area. You could even spend more time in Maine and continue north from Portland to check out Boothbay Harbor and Acadia National Park. If you go up to Acadia though, you probably won’t have time to do much in NH. If you have any questions about anything in this area, do not hesitate to ask! I can give you other recommendations depending on your interests and what you want to see as well.
Awesome suggestions. Thank you!
I'm a big fan of making it up to Vermont. In September, there should be some pretty cheap ski lodges in the Stowe area. Theres a bunch of breweries/ciders in Burlington and Stowe. Some great hikes. Ben and Jerry's, Green Mountain Coffee, Cabot cheese, and King Arthur flour all have factories/stores/tours either in the area or on the way. The downside is that there is enough stuff for you to spend all your time there rather than seeing several closer areas. It might be better suited to a second trip if you come back later.
It really depends on what you want to see and what you like to do. Some other ideas:
Super helpful. Thanks! Question - is it a pretty windy drive to Vermont?
From Providence, yes. I presume it’s about the same from Boston. Lots of state highways and backroads until you hit Keene NH. Shortly after that though, you jump across the river and are in Brattleboro (which is one of my favorite spots in southern VT)
New England does have a lot of windy back roads. From what I remember (and depending on where you are starting out), you would take 89 up all the way to Burlington. Its a highway, but not a particularly big one.
What a great idea! September is a wonderful time to visit New England. Boston is a very walkable town with tons to see, I know there's a lot of guides to travel there but my personal recommendation is to check out Harvard Square, and walk from there to the Harvard Natural History museum. A few other Harvard museums are nearby but that one was my favorite. The walk there is also beautiful with lots of mature trees and historical and interesting buildings.
After Boston, you might want to swing by Salem, MA to visit "witch city". There's a lot of witchy and occult themed shops and activities there and in late September they'll be gearing up for Halloween. You might also consider stopping in Gloucester to see Hammond Castle and then taking 133 back to 95 through Ipswich. Stop at Russell Orchards and try some cider donuts, and if you feel like another stop you can check out the Crane Estate.
Once you connect to 95 you can head up to Newburyport where there's a market street full of interesting little shops and a couple of beautiful parks: Maudslay and Plum Island. You can also go whale watching or catch a boat tour.
When you're done exploring, head up to Portsmouth, NH and check out some of the restaurants there. It's a beautiful historic seaside city with more interesting little shops and fantastic food. I recommend the Puddle Dock restaurant, or Cure for fancier fare, or for more casual try the Roundabout Diner or the Friendly Toast. Strawberry Banke is a popular destination, it's a collection of historic homes with costumed reenactors and some museums. Personally I would skip it and just visit Prescott Park, unless you're particularly interested in history. Then take a walk down market street and grab some ice cream from one of the local shops: Kilwin's, Annabelle's or Red Rover if they're open, you really can't go wrong. Basically, go to Portsmouth hungry!
Once you're stuffed you can get back on 95 to head to Kittery, and if you like outdoorsy goods check out the trading post. There's also a lot of swanky shopping there like LOFT and Coach and other higher end outlet stores. If that's not that interesting, take a little trip up route 1 and visit the aerial adventure park on your way up to York. Once there, you can enjoy the beach and more seaside attractions in town or visit York's Wild Animal Kingdom.
After that, you can either stay on 1 to take your time visiting towns like Ogonquit or Wells, or hop back on 95 and head to Portland. Other posters know Portland better than I, I don't personally know that area as well, but I can say that if you decide to make the trek, Acadia is gorgeous and worth it. Nearby Bar Harbor is also a quintessential New England town and a major tourist hub with more great food.
Ok now I'm done XD
Thanks! Great recommendations.
Take a look at Route 1 along the coast to go from Boston into Maine. It's basically the scenic version of I-95.
York Beach is a cool spot to stop at on the way.
Portsmouth, NH is a yuppie shithole, but the park is pretty and as far as tourist traps go, some folks love Strawberry Banke Museum.
Salem, MA lacks the charm it used to have, but the House of Seven Gables there is still pretty cool.
The Kancamagus highway is also a killer scenic drive through mainland New Hampshire. It's got a few cool stops to hike around at, if you're into that.
It’s been a while since I’ve visited either place, but I remember Marblehead being a nice part of the coast to see and Salem being a good (if packed with kitsch) brief stop afterward.