Brookline is served by three branches of the MBTA (the T) Green Line light rail.
Take the C line from Boston, and get off at one of the main stops in Brookline. Coolidge Corner is a great place to get off the train.
The D line, also accessible from many places downtown, will bring you to Brookline Village, a quaint area with many restaurants, though it isn't as big a draw for people who live outside the area.
The B line doesn't actually enter Brookline proper, but its Commonwealth Ave. stops are all within blocks of Brookline.
The D line is much faster with less stops than the B and C lines. If given the choice between one or the other, take the D line.
All MBTA trains are now $2.50 inbound or outbound ($2.00 with a plastic "Charlie Card").
If you are disabled, think carefully before taking the train into Brookline. Only a few Green Line stops are wheelchair-accessible (the MBTA website should have the most current accessibility information). During busier times of day wheelchair users should have little difficulty getting to Coolidge Corner, Washington Square, and Brookline Village on one of the newer Green Line trolleys with low floors; however many older-style cars with large steps up are still in use, especially during non-peak hours, and these are accessible only via hand-cranked wheelchair lift. The situation is better now than it was even just a few years ago, but the Green Line is still a long way from being universally accessible. The other rail lines in the MBTA, for the most part, have handicap access.
Cars and Brookline, like most of Boston and its immediate suburbs, do not mix perfectly. One thing to be aware of is that there is generally no overnight parking on streets; those cars on streets after 2AM (11PM in some areas) will be ticketed...seriously! There is also a two-hour parking limit, which is not as strictly enforced. (But wouldn't you know it, your car will be the one that gets ticketed :)
Brookline has no navigable bodies of water along its borders. Therefore one cannot arrive in Brookline by boat. Theoretically one could cross the Muddy River by canoe or raft and in doing so travel from Boston to Brookline via boat... but that would be just plain silly.
Coolidge Corner - A shopping area with much to do. Is the most happening area in Brookline. On C Line, Coolidge Corner Stop.
Brookline Village - A somewhat sleepier historic area with many restaurants. On D Line, Brookline Village Stop.
Washington Square - Local shops and some popular restaurants and taverns. On C Line, Washington Square Stop.
Brookline Hills - Around the high school and across Route 9. Very residential. On the D Line, Brookline Hills stop.
Cleveland Circle - Actually in the Boston neighborhood of Allston-Brighton, but is right on the border with Brookline. Large student population, due to its proximity to Boston College. Has some bars, restaurants pizzerias, but is slightly more run-down than Brookline proper (although gentrifying). The intersection is very confusing, as it is the intersection of three different lines of the T. On C Line Cleveland, Circle Stop. On D Line, Reservoir Stop.
Putterham Circle/South Brookline "Chestnut Hill" - Suburban and residential feel. Putterham Circle has a variety of shops, including market, restaurants, bank, hair salon, gift shop, Starbucks, and others. Does not have access to a train, but the Route 51 Bus can be taken to and from Cleveland Circle.
St. Mary's- Overshadowed by nearby Kenmore Square and the Landmark Center in Boston. The area has a little bit to it. Is On C Line, St. Mary's Stop, On D Line, Fenway Stop.
Pill Hill/The Point - Residential area to the south of Route 9. Ritzy. From this area, one can either walk to the Brookline Hills or Brookline Village stops on the D Line, or take the Route 60 bus.
JFK Crossing - Stretch along Harvard St. with a heavy Jewish influence, from just north of Coolidge Corner to Commonwealth Ave. in Allston.
The primary way to get around in Brookline is to walk. Most places of interest are close together, or if you need to go farther away, a short ride on the MBTA will do it. If you choose to drive, be aware—especially on Beacon Street, where the trolley runs down the middle of the street. If one is required, cabs can be easily flagged down on the main streets, and are oftentimes parked curbside waiting for fares at busier hubs (e.g. Coolidge Corner, Brookline Village).
Larz Anderson Auto Museum, 15 Newton Street, Phone: +1 617-522-6547, Fax: +1 617-524-0170, . Tu-Su 10AM-5PM. $5/$3 students and seniors, under 6 free.
John F. Kennedy National Historic Site, 83 Beals St., Phone: +1 617-566-7937, . W-Su 10AM-4:30PM. The 1917 birthplace and boyhood home of the 35th President of the United States. A peek into how people lived in 1917.
The Coolidge Corner Theatre, 290 Harvard Street, Phone: +1 617-734-2501, recorded info:, +1 617-734-2500, . A charming, old fashioned movie theatre that plays art house films, as well as some crowd-pleasers.
Larz Anderson Park, 25 Newton St., ☎ (617) 739-7518. This features an outdoor skating rink, and is the #1 sledding destination in the town. The park is a great place for kids.edit
Brookline Golf Club at Putterham, 1281 West Roxbury Parkway, ☎ (617) 730-2078, . Public 18 hole golf course.edit
Brookline is home to some of the best public schools around. Brookline High School has many famous alumni including Theo Epstein, the former General Manager of the Boston Red Sox and current President of Baseball Operations for the Chicago Cubs; Michael Dukakis, former Massachusetts Governor and 1988 Democratic Presidential nominee; Robert Kraft, current Patriots and Revolution owner; Conan O'Brien, TV host.
J.P. Licks, 311 Harvard St., Phone: +1 617-738-8252, . Sure, there are a few JP Licks in the Boston Area, but this one is still worth visiting. Incredible ice cream, cool neon decorations, and coffee when it is warm.
Clearflour Bakery, 178 Thorndike St., Phone: +1 617-739-0060, . M-F 8AM-8PM, Sa,Su 9AM-7PM. Delicious, authentic baguettes and boules, batards and loaves made fresh daily.
Anna's Taqueria, 1412 Beacon St #1, Phone: +1 617-739-7300. AND 446 Harvard St., Phone: +1 617-277-7111. Has a cult following. Great for some of the most authentic Mexican food anywhere in the United States. Very cheap and fast, and made right in front of you.
Boca Grande, 1294 Beacon St. at Pleasant Street, Phone: +1 617-739-3900. A rival to Anna's for Mexican food.
Coolidge Corner Clubhouse, 307 Harvard St., ☎ 617-566-4948, . Mon-Fri: 11:30am to 1:30am; Sat-Sun: 8am to 1:30am;. Serving the community for over three decades, The Coolidge Corner Clubhouse is a Cozy sports bar with tons of televisions and a large selection of domestic and imported beers. Their food and drinks include 36 Microbrews on tap, Boston's largest Martini Menu, a huge dinner menu including 50 different sandwiches, 20 different Mexican food items, 30 different appetizers, over 40 different salad options, and a brunch menu that offers 18 items to choose from. The Sandwiches, named after Boston sports icons, include a Roger Clemens grilled chicken sandwich with broccoli, honey mustard and melted cheese. Also has 20 HDTV's and shows every NFL Game. Kitchen is open until 1:15am.$8-$15. edit
Pino's Pizza, 1920 Beacon St. #A in Cleveland Circle, Phone: +1 617-566-6468.
Emack & Bolios. 1663 Beacon St. in Washington Square, Phone: +1 617-731-6256, . Su-Th 11AM- 11PM, F,Sa 11AM-11:30PM. Ice cream joint that is a popular hang out.
Brookline Family Restaurant, 305 Washington Street in Brookline Village, Phone: +1 617-277-4466. Daily 7AM-11PM. Great Turkish food for cheap. Definitely try the donar kebab sandwich. Dinner entrees are $10-15 but can easily serve two (or provide one person two or three meals worth of leftovers) and you can really fill up on the bean salad (fasooleeye piaz) and bread that are served with all meals. Go when you're hungry!
Michael's Deli, 256 Harvard St. in Coolidge Corner, Phone: +1 617-738-3354. Go for the corned beef sandwich or the excellent egg and cheese bagels.
My Thai Cafe,404 Harvard St, Brookline, MA 02446, +1 (617) 739-8830. Delicious Asian vegetarian restaurant.
The Upper Crust, 286 Harvard St (Coolidge Corner), ☎ (617) 734-4900, . Thin crust pizza.edit
Wings Over Brookline, 477 Harvard St (North Brookline), ☎ (617) 264-9464, . Chicken wings.edit
Golden Temple, 1651 Beacon St. (Washington Sq.), Phone: +1 617-277-9722. Offers fancy Chinese food with valet parking, and easy access to the MBTA public transportation.
Rod-Dee Thai Cuisine, 1430 Beacon St., Phone: +1 617-738-4977. Amazing Thai food. Seriously. There is a lot of Thai food in Boston but this unassuming restaurant, busy most of the day, may be the best out there. Only a couple of tables, so plan on taking out.
Zaftigs Delicatessen, 335 Harvard St (Coolidge Corner), ☎ (617) 975-0075, . 8 AM - 10 PM. Non-Kosher, "new Jewish"-style restaurant.edit
Fugakyu, 1280 Beacon Street (Coolidge Corner), Phone: +1 617-734-1268. Some of the best sushi in town. It truly lives up to the meaning of its name, "house of exquisite excellence." Don't worry about bringing people who don't like sushi, as they have an extensive menu (many pages) of cooked food and appetizers including shabu-shabu, tempura, katsu, sukiyaki, teriyaki, along with plenty of vegetarian options. There are many private dining rooms for 4 to 20 people that can be requested at the door for smaller parties - reservations are only made for larger groups, along with a large number of open-floor tables.
The Fireplace, 1634 Beacon Street (Washington Square) Phone: +1 617-975-1900, . Creative, modern American cuisine, with excellent, often locally-sourced ingredients. Live music on Wednesday and Thursday nights. Good, all-American wine list in keeping with the menu. Outdoor seating is available during the warmer months, great for people-watching.
La Morra, 48 Boylston St. in Brookline Village, Phone: +1 617-739-0007, . Northern Italian food.
Taberna de Haro, 999 Beacon Street, Phone: +1 617-277-8272. Spanish Tapas at St. Mary's.
Rani Indian Bistro, 1353 Beacon St, Phone: +1 (617) 734-0400, . A distinct step above the usual Indian restaurant. Delicious.
The Capital Grille, 250 Boylston St. (Chestnut Hill), ☎ (617) 928-1400, . Steakhouse.edit
Harvard St. between Commonwealth Ave. and Beacon St. is a heavily Jewish neighborhood: the majority of the kosher restaurants in the Greater Boston area can be found here. These restaurants are best accessed by the 66 bus, although they are within walking distance from the Harvard Ave. stop of the B branch of the Green Line and the Coolidge Corner stop of the C branch of the Green Line. Keep in mind that like most kosher restaurants, these restaurants are closed Friday night and only open late Saturday night (if at all on Saturday) due to the Jewish Sabbath.
In addition to the restaurants listed here, the J.P. Licks mentioned above is also kosher. 
Cafe Eliat, 406 Harvard St., Phone: +1 617-277-7770, . One of the few places to get kosher pizza.
Jerusalem Pita and Grill, 10 Pleasant St., Phone: +1 617-739-2400.
Kupel's Bakery, 421 Harvard St, Phone: +1 617-566-9528. Not a restaurant, but good for a bagel or a light snack.
Rami's, 324 Harvard St., Phone: +1 617-738-3577. A falafel place run by Israelis: has some of the best falafel in the area, with a warm staff who are happy to offer samples and conversation. There are a few tables that fill up quickly at peak times.
Matt Murphy's Pub, 14 Harvard St, +1 (617) 232-0188, . Consistently rated as "Best Irish Pub" by several local publications, this Brookline spot (ride to Brookline Village on the 'D' Branch of the Green Line - about 20 minutes from downtown Boston) boasts fantastic Irish food miles removed from standard pub fare and bartenders and waitstaff with genuine brogues, as well as live music.
The Publick House, 1648 Beacon St. in Washington Square, Phone: +1 617-277-2880, . Has great food and a huge selection of artisanal beers on tap and in bottles. Get your hard to find European beers and domestic micro-brews here. Come for the beer, stay for the mac and cheese and the Belgian-style frites.
Washington Square Tavern, 714 Washington St, Phone: +1 617-232-8989.
Courtyard by Marriot, 40 Webster St. Coolidge Corner, Phone: +1 617-734-1393, Fax: +1 617-734-1392, .
Holiday Inn Boston-Brookline, 1200 Beacon St., Phone: +1 617-277-1200, . The Holiday Inn hotel in Brookline, MA offers an indoor heated pool, fitness center, business center, hotel bar & lounge, and event facilities.
The Beech Tree Inn (Brookline, Massachusetts B & B), 83 Longwood Avenue, ☎ 800-544-9660, . checkin: 2 p.m.; checkout: 11 a.m.. The Beech Tree Inn Bed and Breakfast offers 10 guest rooms in the outskirts of Boston. The inn is just a short tram ride from many of the cities events and activities.Rooms:$89 - $179. (42.340894,-71.117050)edit
The Best Western Terrace Inn, 1650 Commonwealth Ave., ☎ +1-617-566-6260, . Free parking.edit
The Bertram Inn, 92 Sewall Ave, ☎ 800-295-3822, . checkin: 3pm; checkout: 11am. Pet Friendly!edit
The Samuel Sewall Inn, 143 Saint Paul Street, ☎ 888-713-0123, . Known for its warm, comfortable ambiance and spacious guest rooms, it's 14 Victorian-era rooms offer guests a relaxing respite outside of Boston's busy city center.edit
Greater Boston uses 10-digit dialing. This means you need to include the area code whenever you are making a call. The standard area code is 617, but some phone numbers, especially cell phones, use the new 857 overlay.
The town is incredibly safe, with an impressive police presence. Pedestrians entering Brookline for the first time from some of rowdier sections of Boston that border the town often speak of a noticeable change in atmosphere; there are fewer drunks and homeless people, more police, and the beer cans and cigarette butts that line the sidewalks of neighborhoods like Allston disappear. The town works very hard to keep it this way and police can be aggressive. Police in Brookline will often annoy the local high school and college populations for "rowdiness."
This is a usable article. It has information for getting in as well as some complete entries for restaurants and hotels. An adventurous person could use this article, but please plunge forward and help it grow!