MIT lectures, Plough & Stars, Lilypad...

Some options off the top of my head:

Head into Boston (redline is cheap) on a nice day it’s a pretty nice walk. You can walk or use the train to get to a ton of places.

Go to the Boston public library and explore a bit. It’s a really cool old library that is downright beautiful (and free)

Explore the north end (mostly Italian area), if you want to play tourist get a pistachio macaroon at Mikes bakery and a “lobster tail” pastry at Modern pastry. Get a coffee from anywhere else (my favorite is cafe paradiso but I’m sure there’s better). Go and eat your treats and drink your coffee in the green spaces around the north end. Best pizza here: pepperoni pizza Regina’s on thatcher. Best sandwich: Italian from Monica’s (but the owner kind of sucks). Best cheap lunch: galleria umbertos on Hanover st.

If you like sports Fenway does tours and is cool to see in person. If you’re coming next month you won’t be able to see a game but still cool to see in person. The Celtics and bruins are going to be hard to find cheap tickets, but you can sometimes get cheap tickets from the scalpers if you’re only looking for 1 ticket and it’s soon after tip-off/puck drop.

On a rainy day check out the Harvard natural history museum. Harvard square has become a little corporate, but there’s some cool history still around. If you smoke tobacco of any kind, leavitte and pierce is a fun old school shop to check out.

Cambridge/Somerville/Boston are all easily accessible from Kendall. Explore and report back on favorites!

What are your interests? That would help in suggesting stuff catered to what you might like.

The Art of the Brick Lego exhibition on Newbury Street in Boston, any of the Harvard Museums, take a trip to Salem to poke around and visit the Peabody Essex Museum. Learn about the Gardner art heist through podcast, books, movie, and newspaper articles and then go visit the Isabella Stewart Gardner museum. Arnold Arboretum and Larz Anderson auto museum are pretty close to each other so could do both on the same day. Red Velvet Burlesque or Boston Beautease show. Harbor Cruise. Lots of great hiking in The Fells or Blue Hills. Tons of great walking tours in Boston. Take a ferry to P-Town and explore. Get to Plymouth for a day but don’t be surprised by how small Plymouth Rock is. JFK Presidential museum and Library

The toad in porter square, check out their insta page for music lineup. Live music almost nightly.

If you're into ramen or udon, yume ga arukara and yume wo katare are two spots in porter to check out as well.

All of the above very Accessible from the porter redline stop.

Also, definitely take walk across the Longfellow bridge into Boston, stroll through the North End and down towards the Fenway neighborhood.

Museum of Fine Art Harvard Art Museum Read up on the heist and then check out the Isabella Stewart Gardner Museum

Echoing above comment, what are you into?

From Kendall/MIT, walking along the Charles is nice, and there are great walking paths. If you stay on the Cambridge side, you have great views of the Boston skyline. If you go to the Boston side, there’s more things to do in the parks along the path (a beer garden, some docks, etc). You can walk down to lechmere/museum of science and then walk back towards Kendall via Cambridge street (Curio Coffee has great coffee and amazing Liege waffles) to Cardinal Medeiros. State park is great bar near Kendall, Vincent’s nearby has great food.

If you like arcades, A4cade over on Mass Ave (speakeasy/non obvious entrance inside Roxy’s grilled cheese) is a nice barcade.

Just slightly further walk is Backbar in Union square - terrific cocktails, and small/intimate joint where sitting solo at the bar is nice people watching or engaging with bartenders.

Yume wo katare is a spectacular and unforgettable place to dine alone. You are encouraged to eat in silence and ponder your dreams. It is actually stadium seating so everyone faces forward to discourage too much talk. When you finish your meal they will offer you a chance to share your dream with the whole restaurant.

Get a BlueBikes pass and enjoy the growing network of bike paths. At the moment I’m enjoying lunch and a beer at the Notch Biergarten, directly accessible from the paths along the Charles river. I’ll be heading home to North Cambridge via the trail from the Arsenal (open-air mall with some interesting spots) to Fresh Pond, then on to Alewife.

From Kendall you can do the same along either side of the river in either direction. There are great paths through North Point (Lamplighter taproom is a nice spot) then over the roller coaster bridge to Paul Revere park, through the locks to the North End and a nice separated bike lane all the way to the harbor.

The Druid in Inman Sq, and the Burren in Davis, are good for Irish pub stuff. Druid has truly excellent shepherd's pie.

The ICA can be good, although it's a bit pretentious.

Look for discounts to get into the MFA, there are a bunch of different weird offers (like, free for people with Visa credit cards one Thursday a month, that kind of thing.)

I think the Isabella Stewart Gardner museum is free if you're named Isabella. It's a pretty different sort of museum than most places and the atrium is truly beautiful especially when the weather is terrible. Worth a visit even if you don't have a discount IMHO.

If you're doing sandwiches in the North End I say go to Salumeria Italiana on Richmond Street

in the North End, check out Cantina Italiana, I believe it's one of the oldest if not the oldest Italian restaurants over that way, and it's truly a solid restaurant, food and service and all

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also laser floyd at the museum of science, close by to you

ISG FTW!

If you are into craft beer, go to Trillium. It is expensive, but it’s some of the finest New England style IPA in the country. Other styles are good there too, but you have to at least try their IPAs (there are countless minor variations that are all very similar, you can’t go wrong).

If you get access to a car (make a friend!) take a drive to Treehouse for beer too. For a long time there was just one location and it was the only place to buy it. Now there are a handful of locations but all are outside of Boston.

If your username is anything to go by, I'd recommend Darryl's Corner Bar & Kitchen. I really like this spot. But have not been there since the pandemic started.

From Kendall it's almost like a straight 30 or 40 minute walk down Mass Ave. Or you can simply catch the No. 1 bus. (https://www.mbta.com/schedules/1/line). Or just Uber it. With the subway you would have to change lines (Red to Orange). I think the Mass Ave stop on the Orange Line is the closest stop.

Good food, drink, music and people:

https://www.yelp.com/biz/darryls-corner-bar-and-kitchen-boston

MIT museum is fun if you are interested in science and engineering stuff

Absolutely!

MIT also hosted rock/psychedelic shows in the past...not sure if its happening anymore.

The walk across the Mass Ave bridge is by far my favorite skyline view. You get a wraparound view of Back Bay, Downtown, and Kendall Sq skylines all together. Epic at sunset

A little corporate? Every building is owned by one of 5 companies and the only stores they rent to are banks or luggage stores lol. The whole place feels like a dead mall with the food court still open.

If you don't feel like traveling far for a good dinner, both Batifol (French) and Sumiao (Hunan) are solid options in Kendall Square.

Well there is an awesome walk or bike ride along the Charles river on the CAmbridge Side. You can go about 13 mile up but you can see the sky line, water view and its safe and peaceful. Harvard Square is a good walk through. You can explore both MIT and Harvard Yard.

Food: The best Barrito \Mexico is still Filipies in Harvard Sq- they went up in $ and down in quality since covid but stiil the best -about $9 for a burrito. Fish on Wednesday go to Courthouse Fish market on Cambridge St. $10 for fresh haddock and fries. - wednesday special.

Yume wo katare is an awesome ramen place in Porter square. If you don't go early there's usually a bit of a line.

If you're looking for a nicer dinner, you definitely should check out Sarma -- https://www.sarmarestaurant.com/ -- undoubtedly the best food in Cambridge (and in my opinion the whole Boston area).

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It's very difficult to get a reservation, but the "secret" beta is that they have a ~20 seat bar that is not reserved - usually very doable to get a seat on a weeknight, especially as a party of 1. They serve the full menu at the bar and it's a great experience. Can't recommend it enough!

Freedom Trail is really a must as a Boston experience. Boston as a whole is still one of the most segregated communities, so I'd also be remiss if I didn't encourage you to visit and patronize the businesses in the "lesser traveled" areas; Dorchester, Roxbury, Mattapan (someone already mentioned Darryl's).

As mentioned JFK Museum is pretty nice, a bit further out but worth the trip. Of the other museums, Isabella Stewart Gardner gets my vote.

Castle Island (not actually an island) for a lovely walk by the water.

The Boston Harbor Islands (actual islands) are also great for a day-trip.

He said he’s male, which reduces (but does not eliminate!) the chances he’s named Isabella. However, a more universal tip is that if you wear a Red Sox hat (or shirt, or any paraphernalia) you get $2 off!

Felipe’s is one of the few remaining saving graces in Harvard Square, but I can’t resist expressing some El Jefe’s appreciation. The base cost is a bit more, but they up charge you for fewer things (nicer if you like adding “everything” to your bowl/burrito). And they have fried plantains as a topping. IMO can’t go wrong at either place.

Some stuff I (mostly) haven’t seen mentioned yet:

• Check out the schedule at the New England Conservatory (necmusic.edu) - they often have student and/or faculty recitals for cheap or free. If you can find anything happening in Jordan Hall, I’d highly recommend going to it, as it’s a gorgeous, historical performing venue (google “nec jordan hall” for images); note: the NEC is a top-tier music school in the country (oldest music conservatory in the USA), so you might find that worth touring around.
• the Sanders Theater at Harvard is also a nice, “historic” theater, and has some good events; not usually cheap, though. I’m not sure which is actually smaller, but Sanders feels smaller than Jordan
• Harvard Square has been getting bought out by big money, and has lost most of its local flair. Some remaining local places: Black Sheep Bagel, Orinoco (Venezuelan food), Club Passim (live mic/folk, many events), Shays (bar/pub), Whitneys (bar/pub), Charlie’s (pub/restaurant; home of the double cheeseburger!)
• Harvard Square not strictly local but long-standing institutions: Felipe’s (mentioned in other comments), El Jefe’s, LA Burdick’s (chocolate cafe—get their dark hot chocolate! Or any, but the dark will drop you)
• Harvard Square non-food: The Coop (Harvard’s official bookstore, not fun anymore but the sell the Harvard paraphernalia all tourists want), The Harvard Bookstore (independent; not part of the coop; many events, check their calendar!)
• Harvard Square Other: explore the Smith Center and appreciate their relative new renovation with the “living plant walls” and interior outdoor atriums, explore the funky shops/eateries in the Garage (though now it’s mostly Newbury Comics on the second floor; I like the Vietnamese and Indian/Nepalese places on the first floor, though); I didn’t consider/mention spendier places like Harvest (tends to be where visiting dignitaries seem to eat)
• Harvard Square outskirts: Longfellow House and Brattle Street Mansions.. walk by old Tory money, including the house George Washington commandeered to use as his command center for the Boston Siege (operated by NPS, tours; but you can always explore the grounds including a very nice garden in the back); Mount Auburn Cemetery - first “garden” cemetery in the US; served as a model for intentionally landscaped cemeteries worldwide; really pretty grounds with a gothic-looking(?) chapel and also a tall hill in the middle with fantastic views all the way to downtown Boston. If it’s in season (April-October), you can get an even better, more 360 degree view by climbing Washington Tower on top of the hill. Longfellow House is probably a 10 minute (or less) walk from the Harvard T. Mt Auburn Cemetery is a bit further, but still walkable, less than 30 minutes (and it’s a scenic walk down Brattle/Mt Auburn). Note: if you come in mid-late April, on Sundays (and maybe Saturdays..we’ll see if they keep doing that in 2023) they close the busy, multi-lane “closest thing to a highway in Cambridge” street called Memorial Drive. Not the entirety of it, but a good chunk, with Harvard’s campus being mostly in the center of the closures. It becomes a pedestrian park.
• If you’re a gamer, see if you’ll be here during PAX East and consider picking up badges for that huge event

Doh! I should read more carefully. I didn't know about the Sox thing, that's good advice.

This is a good list. I’d also google for harbor tours. Boston is gorgeous from its harbor.

Too bad it’s too early for a whale watch

Literally came here to say that Harvard Square is essentially a mall now. The soul of the square died when they got rid of the ABP.

Same.

But it’s the Harvard Bridge. Named for John Harvard.

Ferry to Salem is great if you have the time for the Peabody/Essex

Does the Druid still have the best fish and chips in the area? I used to love going there on a slow Friday afternoon

Second! Make sure you hit up a pot dispensary first!!

SARMA IS AMAZING!! Sitting at the bar is awesome. Make sure you say “yes” when they bring out the fried chicken!!

I've been told so! Haven't had it in ages so I can't confirm for sure.

There’s a great new book out about Harvard Square and in her forward the author talks about all of this in a really succinct and interesting way.

What’s the title?

the Middle East cafe!

great food and five separate rooms (3 separate restaraunts) with great live music in each one!

I didn’t like the off the beaten path tour, overrated and not good value

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The Fenway Victory Gardens