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Boston/New England in the fall

My husband and I are taking a trip to Boston in early October. We are looking for things to do in Boston and surrounding New England areas. Any suggestions would be appreciated: restaurants, B & B's, hotels, must do's, etc.

Posted by
3933 posts

After numerous trips to Boston, we finally walked the entire Freedom Trail, which was nice and took about 4 hrs or so.

Isabella Stewart Gardner museum is interesting. Quincy Market area is always fun. We've done almost everything there now!

We enjoyed visiting Portsmouth in NH. We have a friend who runs a lovely airbnb just across the border in Eliot, Maine, near Kittery, about 90 min drive to Boston. If you are interested I can PM you his listing. They do amazing homecooked breakfasts (I never had cold maple lavender 'soup' until we stayed with them), make their own wine & beer (which they are happy to share) and even have lots of beehives and bottle their own honey, as well as having many lavender products available.

Not sure how far into New England you want to venture but North Conway/Mt Washington in NH is amazing. North Conway has some great outlet shopping if this is a driving your own car vacation, as does Kittery in Maine. Mt Washington has great views, and there is a Cog Railway there as well.

Salem is kinda fun. We've stopped in some of the seaside towns, but I can't really recall the names.

If you wanted to venture into Rhode Island we visited Newport and stopped into some of the mansions which was interesting.

Posted by
3111 posts

You don't say how long you are staying but with a week or more I'd position myself near Back Bay and walk everywhere (Freedom Trail) or take the excellent public transportation to nearby places like Cambridge during the day. If you are Museum people, I recommend the Isabelle Stewart Gardner Museum.

For fall foliage trips you'll need to rent a car to head north to New Hampture or Vermont or western Massachusetts. Look on line to see where the best color is showing.

When in New England I eat seafood almost every day, especially the more afforadable and delicious lobster. Lobster roll sandwiches are everywhere. If you have time and a car consider driving out to the Cape or taking the ferry to Martha's Vineyard. I love the fried clams on the Cape.

Posted by
1750 posts

I would definitely recommend going to see/visit Old Ironsides. The crew is dressed in period gear and do a great tour of the historic ship.

Posted by
1694 posts

I recommend the New England Aquarium in Boston. It's a very cool design, and has a room in which you get a great (live) panoramic view of Boston Harbor.

Posted by
914 posts

A friend of mine and I took this walking food tour in the North End (Italian section) last year, and although not cheap, it was an informative and tasty experience.

If you have the time, I'd also recommend a walk through the Boston public library to look at the wonderful architecture and upstairs murals. (See central library tab for tours and events.) If you like afternoon tea, it's a lovely atmosphere.

Posted by
3462 posts

Well , after many , many , years traveling about in New England , my list is virtually endless , so I'll confine my answer , if I can manage to control myself , to a few . Where are you coming from ? If from the west of New England , there are many worthwhile stops on the way to Boston , please let me know . One wonderful place just north of Boston , is Cape Ann , Massachusetts . Less well known than Cape Cod , it's only forty or so minutes from Boston , and the drive along route 127 starting just outside Salem , takes you through historic and charming places like Manchester by the Sea , Gloucester , Rockport , and Essex . The surrounding countryside should be in Autumn color when you visit . For a roaring good read about this area - Mark Kurlansky - " Gloucester ; The Last Fish Tale " - And a map of the area -,-70.7060748,12z

Posted by
5786 posts

Been a while but the two restaurants I enjoyed were:

Durgin Park in Faneuil Hall, walking distance from our downtown Boston hotel

No Name Restaurant (just hop in a taxi and have them drive you there).

And of following the Red Line.

Posted by
2917 posts

Tell us how long you are planning to be in Boston and how much time you want to spend outside of Boston in New England, or if you are just thinking of day trips. What do you like? History, art, architecture, local color?

Posted by
13105 posts

Reading with interest, as we are thinking of a quick trip in October to visit our daughter who will be starting graduate school.

I have only been to Boston once before, in October 2015. Loved the Freedom Trail, Fenwick Gardens (the actual gardens), and the Gardner Museum ( although it is a bit dark inside to protect the painting). We walked all over and saw Ringo Starr walking down the street toward us with his bodyguard. (He was in town for a concert),

Posted by
21086 posts

In addition to the Gardner Museum, I very much liked the Museum of Fine Art. The two are very close together, but the MFA is very large and the Gardner itself isn't small.

I went to Legal Test Kitchen twice. I liked it a lot, as did my friends. I've never been particularly impressed by Legal Seafoods itself, but LTK had a more interesting menu. However, it's across the channel from downtown in an area you aren't too likely to be visiting.

Flour Bakey has at least two locations in Boston and is superb. The sticky buns are to die for. They also do sandwiches and I think there might be something like an egg mcmuffin at breakgfast time. Probably some salads as well. The menu is on the website.

If you're not a fan of organ meats, check out potential menus carefully. The better Boston restaurants seem uncommonly fond of offal.

Both my recent trips to Boston were in the winter, and there were times when it was extremely windy. I don't know whether that's an issue all year long or not.

Posted by
2353 posts

Definitely a whale watch, drive Cape Cod all the way to Provincetown - stop at the National Seashore and Highland Light.

Definitely check where the best color is when you get there - google "leafpeeping" there are many websites with current info.

Do not forget dinner in the North End and pastry from Bova's.

There are free freedom trail walking tours that are chock full of info -

The Museum of Fine Art is fantastic

Posted by
351 posts

As a Boston resident I have very strong opinions on local restaurants, tho most of my data is about restaurants on the good side of the river. (Cambridge joke)

I'll rustle up my standard list and post back here shortly...

Posted by
2353 posts Cape Cod all the way to Provincetown....
Nightly News reported that dining options in resort areas such as Provincetown may be limited by shortened seasons for want of workers:

There are many year round restaurants on the Cape - yes fewer on the lower & outer Cape than the upper & middle but they are there. Save dinner for a year round town like Falmouth - great restaurants. Skip Hyannis - very built up - shopping mall & big box stores - unless you are a Kennedy fan - you can peak the "compound" - the JFK museum there is well done.

Posted by
286 posts

While in Boston, be sure to spend some time in the North End. One of our favorite 'old stoves' is La Summa, on Fleet St. It's a small place with authentic Italian fare, reasonably priced with lots of locals and not many tourists. When you're done, up about two blocks is Mike's Pastry, which offers some twenty different types of canoli. Regina's is another recommendation if you like pizza; they don't take reservations and there's usually a line around the corner... but it's worth it!!

Posted by
3933 posts

We've done Mike's Pastry a few times, but have also had great goodies (and less of a line) across the street and down a little at Modern Pastry.

A Bostonian told me to skip the hype at Mike's and go to Bova's Bakery, which isn't too far away. It was nice as well and not insane like Mike's. But I've yet to meet a pastry I haven't liked. ;)

Posted by
2353 posts

We've done Mike's Pastry a few times, but have also had great goodies (and less of a line) across the street and down a little at Modern Pastry.
A Bostonian told me to skip the hype at Mike's and go to Bova's Bakery, which isn't too far away. It was nice as well and not insane like Mike's. But I've yet to meet a pastry I haven't liked. ;)

That's funny - Modern used to be the one with huge line of tourists as it was always touted in the guide books! I wonder if they've been replaced?

Posted by
3933 posts

Modern had a line up as well the two times we went, but it seemed a little more controlled than the chaos at Mikes, where it looks like a mob scene once you get inside.

Posted by
3462 posts

While in Boston , you should make a point of seeing some of the magnificent historical architecture - Copley Square with its collection of grand buildings - HH Richardson's Trinity Church , Charles McKim's Boston Public Library ( with the Puvis De Chavannes murals ) and The Copley Plaza Hotel . Also ,not far from there between Copley Plaza and MFA , McKim's Boston Symphony Hall ( modeled on the Musikverein in Vienna ) This hall has some of the finest acoustics in the world , as well as one of the finest orchestras as well , The Boston Symphony Orchestra . AND , here is a map of the area !!!,-71.0760254,18z/data=!4m5!3m4!1s0x89e37a0eeaa36255:0xbd1b9dc5c8e3b848!8m2!3d42.3499239!4d-71.0761075

Posted by
40 posts

You'll be spoilt for choice...Autumn in NE is my favorite. I grew up on Cape Ann...north of Boston. Best chowder, fried clams and lobster rolls in Ipswich Essex Gloucester and Rockport. Beautiful beaches...Cranes, Good Harbor, Wingersheek and Singing Beach. Family run farm stands with apple and pumpkin picking all around the area. Oldest continuous agricultural fair in America is Topsfield Fair and is on early October. Salem has Halloween and events on the whole month of October. Historic houses from the 1600s all around the area....and thats just north of Boston.

Boston city has changed in the last 10 years but in a good way. More farmers markets around the city...the Waterfront has been revitalised with new hotels bars and restaurants. Classic Boston is the Italian N End...historic homes, museums, Freedom Trail.Beacon Hill..MIT and Harvard.. Head of the Charles rowing competition is on in October. Shopping on Newbury and the Prudential. Outlet shops in Kittery Maine and Wrentham MA.

Sports...Red Sox might be still playing in Oct (cross fingers). And the Patriots will be a month into their season. BC football games.

Cape Cod will be much quieter than summer but still worth a look. Beautiful beaches and there are restaurants open year round.

Newport RI is a fun little town...beaches, restaurants and known for America's Cup sailing and the Cliffwalk...mansions of the ultra wealthy of the 1800s.

And of course a of the gorgeous scenery and folliage. Hire a car and just drive... Covered bridges in Vermont and NH. Beautiful White Mountains...N Conway..a scenic drive on the Kangamangus Highway through NH. Maple farms all around VT and NH......amazing maple sugar candy and fresh syrup. Arcadia National Park in Bar Harbour Maine. You'll be able to google where peak foliage is and follow it around. Usually starts in Sept in Maine and far north and moves south through Sept and Oct.

I'll be going back to visit family in early Sept and cant wait! You'll love it! HAPPY TRAVELS!

Posted by
2 posts

Wow! I'm even more excited to go on this trip now that you've all sent your suggestions. Thanks for all the great tips and recommendations!

Posted by
3336 posts

If you are AT ALL interested in history or literature, you must visit Concord, just outside of Boston. I just returned from a trip for which I was given an academic grant to study Thoreau and his fellow writers, thinkers, and abolitionists in that town. That, combined with the revolutionary war history there, make it an amazing destination. The 17 mile revolutionary road leading from Boston to Lexington, and then Concord has a lot to see on the way as well.
If you head south about 90 minutes you can be on the Rhode Island shore - the mansions of Newport and the surrounding islands are simply beautiful. We enjoyed going to the Matanuck Oyster Bar with some friends who live nearby and the whole area is well worth a visit! We were also pleasantly surprised by beautiful Providence - great restaurants and historic sights. The Rhode Island School of Design has a fantastic museum and Brown University, right next door, is a beautiful campus. We loved Seven Stars Bakery both mornings we were in Providence.

Posted by
1804 posts

If there on a weekend and the weather is cooperating, the SoWa Open Market is always a fun place to have lunch. Lots of artisan goods available for sale, art to check out, big lot with many different food trucks, good beers available to wash down your lunch.

If in Cambridge, check out the Harvard Museum of Natural History. Small museum, but very cool exhibits. Some people love the glass flower exhibit which is back on display.

Posted by
351 posts

My estimates for dinner prices are app + entree or entree + dessert, and don't include drinks. I spend way more time on the Cambridge side of the river, so my recommendations are skewed towards Cambridge/Somerville

My side of the river - Cambridge/Somerville – the heading for each section is its neighborhood

Central Square (T stop is Red Line Central)
• Craigie on Main $75-$100 pp (you'll need a reservation or you can line up when they open and jockey for a bar seat)
• Green Street Grill $50 pp

Harvard Square (T stop is Red Line Harvard)
• Russell House Tavern $50 pp
• Mr. Bartleys $15 pp
• Shay's they have food but the main point is patio drinking! If you must eat, get the hummus or nachos, the grilled cheese has salted bread, yummy
• Alden & Harlow $75 pp (you'll need a reservation or you can show up and try for a bar seat – if you get there by 6 bar seats are usually very feasible)
• Waypoint $75 pp Fish fish fish and more fish No sure how necessary reservations are

Porter Square (T stop is Red Line Porter)
• Christophers $15 pp - great burgers, good tap list
• Toad – not a restaurant, cozy live music venue
• Rod Dee (Thai) $15 pp - no booze, cash only, great pad khee mao a few locations
• Anna's Taqueria $10 pp - yummy burritos, fast, cheap, no booze, many locations

Davis Square (T stop is Red Line Davis)
• Redbones $30 pp – ribs, bbq, awesome beer tap list
• Saccos/Flatbread Pizza $30 pp candlepin bowling and really good pizza
• Painted Burro - $30 pp - outstanding tacos
• Foundry on Elm - Hate hate hate this place. Just listed here as a warning to you

Kendall Square (T stop is Red Line Kendall)
• Friendly Toast $20 pp great breakfast all day, fun cocktails (there is now a Back Bay location)
• Meadhall $30 pp I think they still don’t have a website, but they have an amazing tap list and good appetizers
• Helmand $40 pp do not eat here without having the Kaddo (baked pumpkin)
• Mamaleh’s $30 pp - Jewish delicatessan food, fabulous all day breakfast
• State Park $30 pp

Posted by
351 posts

Boston (My estimates for dinner prices are app + entree or entree + dessert, and don't include drinks.)

The other of the river - Boston – the heading for each section is its neighborhood

Kenmore Square/Fenway Park (T stop is Green Line Kenmore)
• Eastern Standard $75 pp great oysters, fabulous cocktails
• Island Creek Oyster Bar $75 pp
• Lower Depths - $10-$15 pp cheap hot dogs, good beer
• El Pelon Taqueria - $10 pp no booze, inexpensive, good burritos
• Boston Beer Works - $25 pp , brewpub, decent sandwiches
• Friendly Toast $20 pp great breakfast all day, fun cocktails (there is now a Back Bay location)
• Sweet Cheeks $40 pp DO NOT skip the Bucket o' Biscuits

South End
• Toro - Tapas!! $75 pp
• Coppa $50 pp make their own charcuterie

North End (T stop is Green Line or Orange Line Haymarket)
• Daily Catch $35 pp (also one in Seaport & Brookline - those two are much bigger than the North End location) omg such good seafood with pasta
• Ristorante Euno $50 pp
• Antico Forno $35 pp
• (just about any North End restaurant that looks busy)

Back Bay / Newbury (T stop is Green Line Copley or Hynes Convention Center)
• Summer Shack $50 pp
• Legal Seafoods $50 pp - lots of locations
• Bukowski $20 pp decent food, great beer list
• Cafe Jaffa $10 - $35 pp great falafel
• Friendly Toast $20 pp great breakfast all day, fun cocktails (there is now a Back Bay location)

Posted by
2353 posts

For old school Italian in the North End - Al Dente on the corner of Salem & Parmenter.