Whenever friends are visiting from out of town (and sometimes from even out of the country!) they always ask me what there is to do around Boston- and the answer isn’t always easy. I mean, what isn’t there to do around Boston? As bustling and as busy as it is picturesque- Boston has something to offer everyone from all walks of life: rich (and sometimes really insane) history at every turn, breathtaking museums and galleries, incredible restaurants, unique shopping experiences, distinguished and esteemed universities, a thriving night life, plenty of space for those focused on fitness to get their workouts on, a top notch music scene and some championship-hoarding sports teams.
Sure, there are the accents (guilty as chaah’ged,) the not-so-friendly drivers, the mind-boggling roadways, or our questionable and unspoken rules when it comes to parking spaces during snowstorms- and there’s always the comparisons to Boston-centric movies like “The Departed” or “The Town” by those outside the city/state who have never stepped foot in or have met anyone from the Greater Boston area before- but the good outweighs the bad. Boston is a city filled with some of the brightest, most colorful, brilliant and strongest individuals on the East Coast who never hesitate to band together to show the nation- and the world- how united we truly are in the tougher, more challenging times (like in the days following the 2013 Boston Marathon bombing,) to the happier, more celebratory times (like the rolling rallys following a championship win!)
I first started spending a significant amount of time in Boston when I was 16/17 and my friends (some of whom had cars that barely ran) and I were eager to stay out late and see what the city- just an hour or so outside of our small and quiet town- had to offer a group of teenage troublemakers. As we grew up, Boston became less of a late night and weekend-only destination and more of a second home- until it eventually became an actual home for some of us. Over the course of just over a decade leading up to now, I’ve become a regular at some establishments and am still discovering new places now and then that open up doors to whole new worlds, possibilities, interests- and friends.
While there are SO MANY places to go and things to see in Boston, I thought I’d compile a small list of the ones- some well-known and others more well-kept secrets- that I frequent regularly and encourage others to visit while they’re in town and are looking for a good time (or good food) without spending a ton of money. I’ve also included some of the more “tourist-y” staples, too- because why not? If you’re in the city- you may as well participate in some good old fashioned local goofiness!
I’m really going to miss this place once I eventually head out to San Diego. I really, truly am.
*NOTE: Please keep in mind that the places I’ve listed are just some of my own, personal preferences. If you’re looking for other options around the city- there are a lot of helpful resources available (including Yelp and some of the blogs listed in my sidebar under “Local Lovelies!”) I plan on doing another, updated post like this somewhere down the line where I’ll include different locations- but for now- these are just a few of my favorites!*
Let’s start with what most people ask me about- the food! I like to cook, but I also love trying new food at new places, too. Many of my friends who visit ask me about Quincy Market- which is one of the more busy and tourist-friendly areas to dine in the heart of the city, but in my opinion- you can get a generic slice of pizza or a bowl of clam chowder anywhere (without having to be in such a crowded space.) For an unforgettable “foodie” experience, all you have to do is head off the beaten path- just a little bit. Here’s some of my usual go-to spots to dine out.
DINING (BREAKFAST/BRUNCH)
South End Buttery (314 Shawmut Ave): Although you might have to wait a bit for a table at this cute corner cafe, I promise you it’s worth it. The food is incredible- the perfect way to start a Sunday morning- and I highly recommend the herb and cheese omelette. It’s my favorite. If you don’t have time to sit and dine, the South End Buttery also has an equally delicious and impressive take-out menu.
Kelly’s Diner (674 Broadway – Somerville): If you’re looking for a classic diner experience (or want to nurse a hangover,) with some delicious food and a really friendly staff- then you just need to head a couple miles Northwest to Kelly’s Diner in Somerville. On those mornings where I want to cheat on my diet- just a little- I come here and scarf down pancakes like I mean business.
Masa Restaurant (439 Tremont Street): If you’re in the mood for a breakfast/brunch with a more spicy flare- look no further than Masa. Their Southwestern-inspired menu is unique, affordable- and hits the spot. If you’re looking for a pre-noon kick, their specialty drinks are worth a taste, too.
Cafe Luna (403 Mass Avenue – Cambridge): For solidified brunch plans with a group of friends, consider making a reservation at the Cafe Luna in Cambridge. Their menu is a teeny-tiny bit pricier, but their pancakes and omelettes are so, so worth it! I’m also a big fan of their chocolate stuffed French toast- which completely satisfies my sweet tooth.
DINING (LUNCH/DINNER)
Assaggio (29 Prince Street): Definitely one of my favorite spots for an intimate Italian meal, Assaggio is located right in the middle of the North End- making it perfect for a romantic night out with someone special or for a quiet get together with friends and some wine. Definitely call ahead to make a reservation to save yourself some wait time!
Taquería Jalisco!
Taquería Jalisco (293 Bennington Street – East Boston): In San Diego, there’s a Mexican food restaurant called Pokez that I LOVE. I always try to stop there whenever I’m in town because their food is authentic and delicious- and Taquería Jalisco is the East Coast version of that. The restaurant is small- but lively- and their menu is expansive and so, so good.
Beat Hotel (13 Brattle Street – Cambridge): I was recently introduced to this fantastic restaurant located in the heart of Harvard Square, but it has quickly become one of my favorites with it’s ever-changing menu of mouth-watering entrees, specialty drink selections, and live jazz and blues performances. They have brunch options that I have yet to try out- but if it’s as good as their dinner menu- I know I’ll be a big fan.
Wagamama (Quincy Market, Prudential Center, and Harvard Square): There’s nearly a handful of Wagamama’s scattered around the Greater Boston area, which makes it convenient when I have a craving for some of their fresh and filling Japanese food but am not quite mentally or physically prepared to deal with the heavy flow of pedestrian traffic around the Quincy Market area. If you’re looking for a couple of menu suggestions, I enjoy the ebi gyoza, yaki soba, yasai cha han- and any of their raw juices.
Boston Burger Company (1100 Boylston Street): I’m a carnivore, and sometimes- I just want to devour a delicious, juicy burger. While the BBC offers chicken, soup and salad selections, too- their burgers are hands down some of the most amazing things I’ve ever tasted. I love the Waikiki Beach Burger and the Green Monstah Burger the most, but they’re all fantastic. Pair them with your choice of wedge cut fries and you are in for a meal you won’t regret or forget.
Grasshopper (1 North Beacon Street – Allston): Vegan. Chinese. Food. That’s really all you need to know. To some, the concept might be confusing and maybe mind-blowing, but trust me when I say that you will never, ever regret stopping here. The food is fantastic and filling without that gross “I think I might die” feeling you get with regular Chinese food orders. I can eat an alarming amount of their veggie chicken fingers and best of all? They offer a takeout option. YES!
DINING (COFFEE/DESSERTS)
Caffé Vittoria (296 Hanover Street): If you’re craving something sugary and sweet while walking through the North End, you may feel inclined to hop into the ALWAYS RIDICULOUSLY LONG line at Mike’s Pastry to wait for one of their famous cannoli- or, if you want to save yourself some time- you can walk just a few feet down the street and stop in Vittoria for a cappuccino, a piece of tiramisu and take in the charming aesthetic of the cafe. I love gathering here with friends here after a night out or sitting down by myself to sip on espresso and catch up on emails when I have some down time. It’s just a lovely little spot.
The Thinking Cup (165 Tremont Street): Bostonians love their Dunkins, and that’s all well and good- but if you’re looking for something bolder and stronger than whatever ice cream flavor infused coffee D&D is cooking up this week- then I recommend stopping by the Thinking Cup (which also has locations in the North End and Back Bay.) Their coffee is rich and their pastries and sandwiches are fresh- making this place an ideal choice for that early morning brew or evening snack on the go.
Crema Cafe (27 Brattle Street – Cambridge): Crema is another gem located in Harvard Square that boasts a pretty good breakfast and lunch menu, but it’s their coffee and pastry/dessert selection that I rave about the most. I always make it a point to grab an iced chai whenever I’m passing through the square or doing some shopping around Cambridge to keep a little pep in my step- and their coconut macaroons are the stuff dreams are made from. So, so good.
DRINKS (THE 21+ KIND)
McGreevy’s (911 Boylston Street): I swear I’m not putting McGreevy’s at the top of my list just because I’m a big Dropkick Murphys fan (Ken Casey owns the place,) but because they have great drinks (the Pineapple Piper is the best,) awesome specials, a friendly staff- and a ton of historical Red Sox memorabilia on the wall (authentic- NOT cheesy.) It’s a sports bar, so if you’re looking to kick back and watch a game with some good food and a hard drink- this is the spot.
The Junction (110 Dorchester Street – South Boston): Southie gets a bad name sometimes, but if you’re not falling for the tall tales and notoriety often tacked onto this area of the city- it’s a lot of fun to explore. I’m not a big beer connoisseur by any means, but I’ve always enjoyed myself at The Junction when I’ve popped in. The service is good and the atmosphere is welcoming- and you’re guaranteed to have a good time if you stop by when there’s any type of sporting event going on.
Tavern at the End of the World (108 Cambridge Street – Charlestown): I love Irish pubs. I love pub food- and I love Charlestown- so TatEotW is a nice stop whenever I’m hanging around Bunker Hill and want to grab some not-so-diet-friendly food and a couple of drinks. This place sometimes has live music and stand-up comedy shows, too- which can be a fun way to end the night.
Highball Lounge (90 Tremont Street): If cocktails (or cocktails with little rubber duckies floating in them) and unique finger foods are more your style, then you’ll love Highball Lounge. With a sprawling space, fancy furniture, board games and occasional live DJs performing- Highball is perfect for bigger get togethers and parties that require a little flare and pizzazz to keep everyone entertained. Also- did I mention the rubber duckies in the drinks? Because I love that.
Sunset Cantina (916 Commonwealth Avenue): In the Summer, and typically before/after I catch a show at the Paradise (more on that later,) I like to swing by Sunset Cantina to grab a margarita and some snacks. This place has such a HUGE menu filled with fantastic drinks and food, and it’s within walking distance from pretty much anything and everything- shops and restaurants, to music venues and the Green Line (in case you have somewhere else you need to be.)
Brick & Mortar (567 Mass Ave – Cambridge): One of my favorite hidden gems in Central Square, B&M lies within exposed brick walls above Central Kitchen. Skilled bartenders mix your poison behind a copper top bar, and the atmosphere is very laid back and relaxed. I like to come here on low-maintenance dates from time to time, and I’m never left disappointed. This is a great spot in Cambridge and worth a visit if you’re in the area.
Jillian’s (145 Ipswich Street): Following shows at the House of Blues down the street, I like to bring people to Jillian’s for a nightcap and some highly competitive pool and/or bowling (highly competitive for me, anyway.) Jillian’s is a three-floor bar equipped with a fully functioning bowling alley. Some nights are busier than others, so I recommend calling ahead if you want to get a couple of games in- but I’ve always had a tremendous amount of fun here every time I’ve stopped by.
LIVE ENTERTAINMENT
When it comes to live entertainment around the city, Boston has all of your needs covered. With an active theater district, a couple of stadiums and arenas for bigger shows and events, and plenty of smaller venues to house independent artists, comedy, poetry, and everything in-between- all you have to do is look- in any direction, really- and you will find a lengthy list of easily accessible places to go to be entertained.
Paradise Rock Club (967 Commonwealth Avevnue): By far my favorite music venue in Boston, The ‘Dise is a small, intimate venue that has played host to some of my favorite rock artists. The sound carries really well throughout the building, so if you’re standing in front of the stage or you’re up in the balcony area- you’re going to have a great view and hear everything perfectly. I have so many fond memories and have met so many friends while hanging out here.
Middle East (472-480 Massachusetts Avenue – Cambridge): This is another smaller venue in Central Square where I’ve seen plenty of awesome shows and have danced ’til dawn during DJ nights. If you can get past the fact that it can get humid and musty in there (it is basically a cellar, after all,) than you’ll have a lot of fun here. There’s also an upstairs area that houses shows and events, and serves food as well.
The Comedy Studio (1238 Massachusetts Avenue, 4th Floor – Cambridge): Boston has no shortage of comedy clubs, but The Comedy Studio is hands down the best- and not just because I worked there for a while, either! Located above the Hong Kong restaurant in Harvard Square, TCS features some of Boston’s funniest stand-up comedians and plenty of talented up and comers every night. They also serve a mean scorpion bowl. Stop by and tell Rick, the owner- that I said hello!
The Cantab Lounge (738 Massachusetts Ave – Cambridge): If you like poetry readings, both watching and/or participating, then you should head over to the Cantab on Wednesday nights where the venue hosts weekly poetry slams. The lounge also serves as a spot for open mics and live bluegrass and blues shows, too- and serves up drinks and food if you’re looking to make an evening out of the trip to Central Square.
Tunnel (100 Stuart Street): I’m not big on going to dance clubs much these days, at least not as much as I was in my early twenties- and many establishments I used to frequent have long since closed. I’ve been to Tunnel, located inside the W Hotel, a few times- and each time has been fun. I like the atmosphere of the club and the efficiency of the bar staff. The space is tiny, but unless you require a tremendous amount of room to dance- you can make it work. There’s also some seating, and VIP tables are available for reservation.
House of Blues Boston (15 Lansdowne Street): Formerly the Avalon and Axis night clubs (R.I.P.) across from Fenway Park, the HOBBoston serves as a multi-floor bar, concert venue, and night club (if you do, in fact, need a tremendous amount of room to dance.) I’ve seen a lot of great shows here since it’s opening, and it’s just a short walk away from other bars, restaurants, cab stands, and the T- which means you can get back to where you’re staying quickly and safely.
STRETCH YOUR LEGS
I don’t tell every visiting friend or family member to sign up for a gym membership in the city if they’re looking to get a workout, because there’s plenty of places to get some exercise that are both free and picturesque. My friends and I pretty much walk everywhere- reserving our cars and the T for when we need to be at a certain place in a hurry (like work or the airport, for example,) but if you’d rather I list a couple of places where you can run/walk/bicycle/stretch in peace- then here you go!
Commonwealth Avenue Mall (484 Commonwealth Avenue): Located right next to the Public Garden, The Commonwealth Avenue Mall is a strip of trees, greenery, and statues that stretches through Back Bay alongside beautiful brownstone homes and businesses. I love passing through this area at night in the warmer months, and I always see people jogging along the pathway or stretching on the grass. It’s just a clean, pretty area to work out.
Chestnut Hill Reservoir (400 Chestnut Hill Avenue – Brookline): If you want to get a nice walk/run in somewhere that isn’t right smack in the middle of the city, then I recommend the Chestnut Hill Reservoir, which is located within a reasonable distance from Boston College but is still tranquil and scenic enough to make it feel like it’s miles away from civilization. There’s wildlife, plenty of greenery, and space to move around.
Castle Island HarborWalk (2010 Day Boulevard – South Boston): If you want to spend a day at the beach without making the drive to New Hampshire or Cape Cod, then Castle Island is a great destination. Sandy beaches, boating, and plenty of space to run/walk or stretch out on the grass and get some sun- this is a nice spot to spend a Summer afternoon.
SHOPPING
Narrowing down places to shop around Boston was almost as difficult as selecting some of the restaurants I listed above. There’s just so many places scattered around the city where you can find pretty much anything you’re looking for. Instead of doing a shop-by-shop list, which would have required an entirely separate post on my blog- I condensed this part of my guide into areas that feature a variety of stores and items for everyone’s tastes and interests. I hope it’s helpful!
Newbury Street (Back Bay): I have a love/hate relationship with Newbury Street. It’s a great mix of high end boutiques (including Chanel, Tiffany’s, and Armani) and affordable shops (Forever 21, H&M, ALDO, etc.) as well as restaurants and bars, but traffic- both auto and pedestrian- is a nightmare. My best advice if you attempt to brave this very busy area is to take the Green Line to Copley or Hynes Convention Center and learn how to maneuver yourself around and between the slow walkers and the groups of people who walk side by side across the sidewalk and block everyone’s path.
If you can’t take it anymore, the shops at the Prudential Center are only a hop, skip, and a jump away!
Assembly Row (340 Canal Street – Somerville): Relatively new, Assembly Row offers a wide array of shops, restaurants, a movie theater, Boston’s LegoLand, and special events like free riverfront yoga classes and weekly outdoor concerts. This place is great to shop in during the warmer months, and has the same charm as Newbury Street without all of the overcrowding.
Harvard Square (Cambridge): I’ve already mentioned a few places around Harvard Square to dine, drink, and see some live entertainment- but I can’t NOT talk about how the square is a great spot for shopping, too. There’s a lot of eccentric little stores and fantastic finds just waiting to be discovered between more well-known shops. I’m a big fan of Raven’s Used Books and Goorin Bros. Hat Shop, but I’m always being introduced to new things whenever I’m in the area.
Garment District (200 Broadway – Cambridge): Boston has plenty of department stores, but if you want something a little more alternative, unique, and affordable- then you don’t need to look any further than The Garment District. Specializing in buying and re-selling gently worn clothing, GD carefully categorizes their inventory to make it easier for shoppers to find whatever it is they’re looking for- from swimwear to shoes, work clothes to Halloween costumes. There’s seriously SO much to peruse through and they are always updating their stock. Every once in a while you can find a great designer piece for a fraction of the cost- so keep your eyes peeled!
TOURIST-Y FUN
I can’t give someone a tour of Boston without taking them to at least one “tourist” hot spot. Let’s be real- Boston has a lot of history and even more famous landmarks. While some people may get annoyed with certain places and areas being overtly crowded with out-of-towners stopping to snap selfies or check a map- I think it’s great. I’m proud of my city and I’m always thrilled that other people are taking time to check it out, learn, and experience it firsthand. I encourage tourism as long as visitors are being respectful of the area and of the locals (so no making fun of our accents to our faces, okay? We know they’re obnoxious.)
Here’s a few places I typically bring friends to get the “Boston” experience.
Fenway Park (4 Yawkey Way): The Green Monster, The Cathedral of Boston, and home of the Boston Red Sox- you have to visit Fenway at least once in your lifetime and you have to catch a Sox game there at least twice in that same lifetime. I love this ballpark, overpriced drinks and all- and seeing a home game doesn’t have to cost you an arm and a leg if you don’t mind standing for a few innings or just want to experience your first real sing-along to “Sweet Caroline.” I buy standing only tickets all the time and enjoy myself just as much as the people in the more expensive seats. It’s all about making the most of the event.
The Freedom Trail (Boston Common): Look, The Freedom Trail is boring. I’m just going to say it now. You follow a red line marked on the sidewalk around Boston for a couple of hours and see some historic sites and that’s about it. I know a guy named Rob who is a tour guide- he wears a colonial costume and everything- and even that’s not enough to get me to go through with this more than once- but if you love history and you REALLY want to see Paul Revere’s house or the Granary Burying Ground- then I say go for it! You’d probably spot these sites while walking to something infinitely more interesting and fun anyway- but by all means- take the tour if you want.
Boston Duck Tours (Museum of Science Driveway): Getting stuck in traffic behind one of these monstrosities is infuriating, no doubt- but I can absolutely understand the appeal of the Duck Tour- especially for those with small children or elderly companions who can’t navigate around Boston on foot quite as easily as others but who still want to see the city. For $35 bucks (adult price) you get an 80 minute tour of Boston- riding around on these bus/boat hybrids that bob and weave through the streets and eventually take a dip into the Charles River while a guide points out places and facts for your listening pleasure.
Cheers (84 Beacon Street): The biggest misconception about ‘Cheers’ is that a lot of visitors seem to think the interior of the bar resembles that of the bar from the television show. It doesn’t. The only thing that is the same is the exterior of the building- but that doesn’t make “Cheers” any less of a fun tourist spot while you’re in the city. With really good food, a lot of memorabilia on the walls, and a gift shop with plenty of assorted “Cheers” themed knick-knacks to buy- this is a must-do while you’re in the city. There’s actually two locations in Boston, but the better of the two is on Beacon Street- in my opinion.
Boston Common (139 Tremont Street): This is actually a spot that both tourists and locals love and appreciate, and is one that I spend a lot of time in on nicer days. Boston Common and the Public Garden- a sprawling park with greenery, sculptures, vendors and areas for live entertainment- is the ideal place to spend an afternoon reading under a tree, having a picnic, playing sports, strolling around, etc. It’s also just minutes away from Downtown Crossing, Newbury Street, the State House, Beacon Hill, and a lot more. I always make it a point to proudly show it off to anyone who is visiting Boston for the first time because they usually fall in love with it right away.
Faneuil Hall (1 Faneuil Hall Square): When passing by Government Center or the Waterfront, I encourage people to admire Faneuil Hall from a distance. It’s lovely to look at but is kind of a mess to walk through unless you’re in the area later on at night after the street performers and vendors have gone home for the day and most of the shops have closed. It’s a very, very packed area for pedestrian traffic, but it’s historic and has some intriguing stores and restaurants if you’re feeling brave enough to face the crowd and uneven cobblestone (wear comfortable shoes!) I do admit I really like this area at Christmastime though, when it’s lit up and the gigantic tree has been set up and decorated. It’s very, very pretty!
Museum of Fine Arts (465 Huntington Avenue): Boston has a lot of great museums, and I would have gladly listed them all- but I wanted to feature my favorite of the bunch and that is the MFA, without question. I can spend hours in this place going from room to room and admiring paintings and sculptures and the new exhibits that are set up every few months. It’s a beautiful space with helpful tour guides and stops to rest, shop, and eat whenever you need a break. The museum also has a lot of special events and offers classes, too. You can get a heads up on upcoming activities and exhibits by subscribing to their monthly e-mailed newsletter.
Boston Harbor (1 Long Wharf): Like Boston Common, I enjoy spending time outdoors down by the waterfront on warmer Summer days. There’s plenty of places to sit and watch boats passing by or grab a quick bite to eat- and if you’re not prone to seasickness- you can always kill some time by catching a harbor cruise or by going on a whale watch. I particularly like bringing my friends from England to this area- just so they know where we threw all of that tea that one time (Hi Imogen!)
And there you have it! My guide to Boston. As I stated above- there’s still SO much more to do and see- but I simply cannot list it all! I thought the locations I linked to were a good place to start, and I do intend to write a follow-up in the future- but I hope that this post is helpful to newcomers who are visiting the area for the first time or who are back again and may have missed some of what I’ve listed.
Are you from Boston? Have you visited? Is there anything you think I should add? Do you have any questions about anything I’ve written about or linked to in this post?
Let me know!
HELPFUL LINKS:
CityOfBoston.gov
MBTA.com
Hotels in Boston
ARTSBoston (includes theater and city festival schedules/tickets)
*IN CASE OF EMERGENCY* – A comprehensive list of hospitals and medical centers in and around Boston.
xx
(All photos included in this post are my own.)
Legally Redhead 