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Every Friday at Jacob Wirth's in Chinatown there is a live piano singalong with pianist Mel Stiller. He's been performing at Jacob Wirth's since 1988 and plays from 8pm-midnight. It's a lot of fun with a group of friends, a table, and some good German food and beer.
A new site called PadMatcher is exclusive to Boston and doesn't have any duplicate listings (doesn't scrape from Craigslist). It's pretty easy to navigate and completely free. You can find roommates on there as well. The address for the website is padmatcher.com.
Right on Boylston St near Prudential/Lord and Taylor is Cigar Masters. It's a great, relatively subdued and hidden place to go and enjoy a cigar while having a drink. They have a big selection of cigars for aficionados and beginners alike. Although they don't have a liquor license you can enjoy a cold beer or wine with your cigar as well.
Every Monday at 6pm, Lululemon hosts a run club event at their store in the Prudential Center. People meet up and go for a 3-8 mile run then go to the Back Bay Social Club afterwards for free appetizers, drinks, and food.
Last year Boston debuted it's bike-sharing program called Hubway. If you're looking to get into commuting by bike or just want to get around the city it's a good deal. For $70/year you can get unlimited rides under 30min, or for $5 you can get a 24-hour membership. There are over 400 bikes in the system now all over Boston and the system will be expanding to over 1,000 total bikes and including Brookline, Cambridge, and Somerville. More information is at http://www.thehubway.com
If you're headed downtown for the night and absolutely need your car you can park at the Post Office Square garage for $9 as long as you're in after 4pm and out by 8am.
If you are looking to go downtown and the nearest T stop to you has commuter rail service (Ruggles, Back Bay, Etc), it's often significantly quicker and easier to just jump on the commuter rail. The trains break down less often, they go faster, and even though it's the same price as the T for inter-city travel they sometimes don't even collect the fares.
Moving companies like UHaul, Penske, and Ryder make a lot of money off local trips. To save money do a one-way trip. For example with Penske a one-way trip with a pick-up at the Home Depot in Medford and a drop-off two days later at the home depot in Roxbury is 60% cheaper than a local rental returned to the same location.
