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Best / most charming place(s) to visit in New England?

6 years ago

Y'know - it's entirely possible I've posed this question in the past, but I can't recall for sure and don't even know when that would have been, so bear with me here. My mother and I have been planning a trip to England in 2020, returning to the wonderfully wonky medieval town of Lavenham in Suffolk, where we've been a couple of times before. Mom will be 80 then and her mobility has declined, so our thought has been to stay in a wonderful cottage that we've already found, and just spend time there in the small town "living like the locals do", more or less. We have a few friends in the area as well, so it would be nice to see them.


Well - Mom recently spent time with a friend who is going to New England with HER daughter, which started both of my parents thinking that perhaps Mom and I should look into NEW England for 2020 instead of OLD England. We have gone to England and other parts of the UK together numerous times, and it's always been "our special thing", but have never visited New England. My recent trip to New York City really surprised me, in that I fell instantly in love with that place, and while my mother and I would likely not go there, it has made me realize that there are surely many places in the northeast that I would enjoy visiting just as much.


Now ... all of this said, if Mom and I WERE to start looking into a week-long (let's say 7 to 10 day) girl's trip to New England for next year, where are the best places to consider? We love charming, old places. The more charm, the better. Anything that would remind us of Old England would be lovely. I'm sure the coastal areas are gorgeous. And time of year ... not sure, but probably late spring to early summer. We would prefer to stay in a self-catering cottage where we can prepare our own meals, and of course, the cuter the better. We would rent a car and drive around seeing the sights.


Is that enough information to go on in order to ask for some area recommendations?

Comments (29)

  • 6 years ago
    last modified: 6 years ago

    FYI, here's the cottage we will rent if we end up doing the trip to Lavenham (UK) next year:

    https://www.airbnb.com/rooms/26080321?adults=1&toddlers=0&guests=1&sl_alternate_dates_exclusion=true&source_impression_id=p3_1558372590_XzOmQcd2IeM4T7xR

    I fear that finding accommodations in New England will prove to be a much more expensive proposition, so that may be one thing that this consideration does not have in its favor. There are some seriously adorbs rentals I've already been able to find though, like this little doll's house in Plymouth, NH.



  • 6 years ago

    I'm partial to Guilford as my family has been going there for the summer for generations. It is quintessential New England- on the coast, lovely town green, beautiful homes and friendly people. The towns as you go further up the CT coastline are equally beautiful (Madison, Mystic...keep going for an hour until you hit the beaches of Rhode Island. Misquamicuitt (I'm sure I butchered that one,) is a fun beach town just over the state line.

  • 6 years ago

    Thanks, jojoco! I'll check into all of those places!


    I'm finding a lot of cute rentals on Cape Cod. Is that a good place to go as well?

  • 6 years ago

    I was going to suggest Cape Cod-- lots of charm.

    jojoco- I live one town over from Guilford.

  • 6 years ago

    Agree...the mansions in Rhode Island are not to be missed.

  • 6 years ago

    I vote for Nantucket.

  • 6 years ago

    Cape Cod is amazing. You can take a ferry to either Martha's Vineyard or Nantucket. The most charming islands.


  • 6 years ago

    Western MA is lovely and charming...Stockbridge is full of museums to tour including norman rockwell, edith wharton's home, naumkeag gardens, chesterwood, ventfort hall, and then head up to williamstown to the clark museum, where the views from the grounds are as fab as the art. Plan it right and you can hit a concert at tanglewood or a performance at jacob's pillow. There's also the hancock shaker village which is fun to see, and I was surprised at what a nice art museum they have in pittsfield ma. If you want a little extra R&R, there's kripalu in lenox where you can get a day pass to attend a lecture on cultivating happiness or, do some yoga, meditation...

  • 6 years ago

    Gosh, so many places to consider. I just looked at Nantucket, and rental cottages (based on Airbnb) are significantly higher-priced than Cape Cod cottages. Admittedly, I know next to nothing about this region, and perhaps that's one reason that it appeals to me -- so much there to be "discovered"! Is Nantucket simply more "exclusive"? Also, how easy is it to drive around this part of the country? I've driven in England a number of times (but vowed never to do so again - it just makes me too uncomfortable driving those narrow little roads with cars parked on both sides, with the steering wheel on the opposite side than what I'm used to), but no idea what to expect in New England.

  • 6 years ago

    Here's another question -- Mom has always loved being in England when things are blooming. Daffodils, snowdrops, crocus in early spring, and the profusion of flowers leading into summer. When's the best time for seeing pretty blooming things in New England? And which area would you say has the "biggest show" of beautiful bloomers?

  • 6 years ago

    Spring (April, May & June) would be the ideal time for blooms. June is when the rhododendrons bloom and those were always a favorite. I would suggest, if you want to get the most of a 7 to 10 day trip, plan on visiting at least 3 central areas in the region staying a few nights at each place. Then you can map out what you want to see during your time in each. I would do a southern New England base (Rhode Island & Connecticut) , a Boston and/or Cape Cod base and then a Northern New England base, NH, VT or Maine. There's so much history and beauty to see in each region, you couldn't possibly see it all. The coast in most if not all of New England is gorgeous.

  • 6 years ago

    Hadn't thought about staying in various areas, but that's a consideration too.


    Found this place on Martha's Vineyard, which looks quite nice to me, and the price seems very reasonable.

    https://www.airbnb.com/rooms/1744563?location=Sandwich%2C%20MA%2C%20United%20States&guests=1&adults=1&sl_alternate_dates_exclusion=true&source_impression_id=p3_1558383175_9CwjsTYjrTmIXTp%2B


  • 6 years ago

    A little guest house in Sandwich:

    https://www.airbnb.com/rooms/14967218?location=Sandwich%2C%20MA%2C%20United%20States&guests=1&adults=1&sl_alternate_dates_exclusion=true&source_impression_id=p3_1558382781_GDbNjEJOMrrjWa8D


    I am seriously swooning at the cuteness available!


    The more I think about it, the more I quite like the idea of dong as durango suggests and basing ourselves for two or three nights in a few different areas. That would be quite a different sort of trip than what we're planning for England (where we won't even have a car), and could be something of a whirlwind tour that could actually be a lot of fun!


  • 6 years ago

    And thank you all for the excellent ideas. I have much to research.

  • 6 years ago

    If you go to Nantucket, you can also take the boat over to Martha's Vineyard. Both islands are fabulous.

  • 6 years ago

    An idea might be to fly into New Haven, CT and work your way up I95/ Route 1. There are so many pretty coastal towns. Charlestown & Newport in Rhode Island. Cape Cod & Boston in Mass. One after another in Maine.. Rockport and Camden are standouts.

    My dh and I used to go to Martha's Vineyard often. Then one trip, we took the ferry over to Nantucket for the day. We never went back to Martha's Vineyard after that. We LOVE Nantucket. Spent many, many fun weeks there. You really can't beat the town for charm, quaintness and cute!

  • 6 years ago

    Nantucket is so charming.

    If you choose New England over old, be sure you won't regret the choice should your mother be unable to make transatlantic trips in the near future. Just a thought. I kno wlong flights can be hard on us as we age.

  • 6 years ago
    last modified: 6 years ago

    Driving in New England is easy in the non-metro areas. It's busy and full of traffic on 95 in CT and 91 in Hartford esp at go to work times and go home times. But 95 out of CT toward the Cape is always a total mess on Fridays....as is the Sunday return. Don't drive in Boston unless you are very comfortable driving in crazy traffic on crazy streets. Better to park in a suburb and take the T (subway) into town and toddle around that way.

    NH and VT have some really cute towns too and lots of beautiful scenery. One of my favorite views is from the back porch at the Inn overlooking Mt Washington...can take the cog train to the top which is a fun ride.

    But I'm still thinking West MA in the Bershires would be fab.

  • 6 years ago

    If you folks are from Texas, I suggest an Autumn visit. Include Vermont.

    ML (a Floridian who is always blown away by Fall Foliage)

  • 6 years ago

    Ida, what do you like to do when on vacation with your mom; shop, drive around, house tours, museums, sporting events, concerts, festivals, aquariums, sit in a B&B and sip tea, walk the beach, swim, boat, etc.? To me, the answer to those questions should drive your destination(s). For instance, if you like house tours, Newport, RI is your place, if you want to walk the beach, Cape Cod, Nantucket or MV are good choices, if you want scenic coastline, Maine, scenic mountains, NH and VT are good options, museums, shows and aquariums, go to Boston, etc.

    I love the gardens at Smith College (western MA), but that's a 2 hour visit, if you want FLOWERS, you should go see Jojoco and visit Longwood Gardens in PA, I'm not aware of any gardens in NE that compare. If you venture to northern NE, April and early May aren't options if you want lots of flowers, I still have daffodils and tulips in my yard (I'm in NNY, but our climate is very similar to NNE) and lilacs are usually just after Memorial Day, southern NE has an earlier spring.

  • 6 years ago

    I’ll throw a few more options at you:


    Portsmouth, NH, and

    Ogunquit, ME

    You can stay in either place and visit the other, as they’re only about 1/2 hr apart. Portsmouth is quaint and historic, and Ogunquit is just a lovely seaside town.

    A little farther north, Portland ME is a great city with soo many great restaurants. You can also take a ferry from there to Peaks Island (easy day trip). So maybe I’d stay half the time in Ogunquit with a day trip to Portsmouth (and Kennebunkport!); then drive up to Portland for the second half of the trip.


    Ogunquit is only an hour or so from Boston, so you could fly into Boston and easily spend some time there too.


    Nantucket is pretty but expensive and I think a lot of the tourists there can be snobby. Sorry, Nantucket fans.


    Newport, RI, is nice too, and from there I’d also recommend driving to check out Tiverton, Little Compton, Portsmouth (RI, not NH), Jamestown and Narragansett (great beaches!). You could also take a ferry to Block Island, which is beautiful.


    Cape Cod is great, just don’t go at the height of the summer. You can easily take a day trip to Martha’s Vineyard from there.


    You might like Lenox, MA, and the Berkshires too! Canyon Ranch?!


    I live near Boston and flowers are just starting to put on a show. April is not reliable for flowers or good weather. June is great! I would recommend June or September to avoid the height of tourist season.

  • 6 years ago

    Some years, May can be pretty chilly in the northeast. My sons birthday is end of May and when he was little we had snow flurries during his birthday party, which was pony rides outside. All the kids had their winter snow jackets on!

  • 6 years ago

    Have you spent any time in Boston? It is a good size city, but doesn't feel that way ... unless you are in traffic!

  • 6 years ago

    Ida, if you are considering either MV or Nantucket, I'd choose the Vineyard. You could be entertained for a week. I'd suggest June thru Sept with a strong pull for Sept. There's a lot going on in July and Aug but the place is crowded. Tons of art galleries, literary events, a wonderful county fair--lots to do. MV has 5 towns each with a different vibe. It's a bit of a pain to get there (having a car on the island gives maximum flexibility) so def make reservations for everything well in advance. But I adore the place and think you would love it too.

    Daytripping there wouldn't appeal to me as much.

  • 6 years ago
    last modified: 6 years ago

    Part of the reason for turning our attention to New England is that the transatlantic journey to the UK is already a difficult one for my mother. Last year we went, and she suffered with a partially diagnosed back problem that actually compelled her to have back surgery the month following our return home. She was in significant pain for much of the trip, but somehow managed to "keep calm and carry on" for the most part. She's over that physical problem now, but realizes that she moves much more slowly than ever before and it's just increasingly hard to get out and do/see as she once was able to. However, England maintains its "magical hold" over us both, so I can't say we've ruled out the trip that we've been planning ... just wanting to weigh all of our options, and it does seem that New England holds a number of good ones!

    As for what we like to do ... Well, we mostly just enjoy the experience of being in new places and seeing how others go about their lives. We are people watchers, and enjoy meeting locals. We like historic places (although we don't tend to spend a lot of time in museums), places that are quaint, charming, and beautiful. We like to dine out -- nothing terribly fancy, though -- and have a fondness for afternoon tea. We like ice cream. We like interesting, quirky shops. We like encountering interesting, quirky people. We like seeing things that are very much unlike things we would see at home.


    I watched a few YouTube videos last night on New England, one in which a man talked about HATING to drive in that part of the country. He said that particularly in the summer and fall, roads are horribly congested, but that some of it can be avoided if one gets off the main drags and heads for the backroads. Is that easily done?

    Re Martha's Vineyard -- I've read that it costs around $140 or so take a car over on the ferry. Does that sound right? Does that include the return trip? Renting a car on MV is prohibitively expensive.


    I have never spent any time in Boston (although I'll be flying through there in a few days). I've looked into flying into other places such as Hartford and New Haven, and it looks like BOS is going to be our only option for non-stop flights on AA.

  • 6 years ago

    Roads are only congested in the height of summer at the touristy areas. IMO the Cape is the worst in that regard. Newport/RI destinations are not as bad. Boston city traffic stinks no matter what, but all of New England certainly isn’t a traffic jam. In beach areas, there will be traffic both from people heading there for the weekend (or week) as well as day trips to the beach. Plan most of your driving for weekdays and you’ll be fine. And avoid rush hour anywhere near Boston!

  • 6 years ago

    Yeah - I was just thinking how the freeway I drive between Fort Worth and Dallas is no cakewalk, and at evening rush hour it's a particularly hellish enormous parking lot. I think if one is USED to traffic, then seeing it elsewhere probably isn't such a big shock.


    Was just emailing with Mom, and she's not completely ready to give up on our England trip for next year; in fact, she's wondering if we could do England next year and New England in 2021. Seems like ages from now -- although I do know it will be upon us before we know it, so it's good to think about these things and start formulating.

  • 6 years ago

    Ferry fare estimate is correct. But I love the ferry ride over, and get very sad on the trip back. The payoff; Edgartown is swanky, Oak Bluffs is gingerbread kitchy, Vineyard Haven is homey, Chilmark is quiet, and Aquinnah is scenic.

    I'd tell you to go to the Flying Horses, Illumination Night at the Tabernacle, The Gay Head Light, Menemasha for sunset and ice cream, and lots more. Easier than a transatlantic flight.

    I had a good England trip with my then 80'ish mom and sisters. We did Devon, Bath, Stratford, and London.