Salted Almond Chocolate Mexicano from Taza: I love that this amazing chocolate is from Boston. Salted almond is my favorite because the almonds are ground down to fine powder (I detest chunks in my chocolate) but cinnamon is a close second, and I'm dying to try their new ginger one. $4.50 for a chocolate disc.
Potted Rosemary Plant: Available at Amazon for $7.99; or possibly available at your local farmstand or nursery.
Boston Biking Pocket Guides: Shop local! I imagine a lot of cities have these, but I do love the ones you can get here. Five rides come in each pack, each one laminated with directions on one side, map on the other - with bike shops and ice cream shops labeled, in case of emergency. Pick them up at REI or at Bikes Not Bombs in JP they're less than $10 a pop.
Theo Chipotle Sipping Chocolate: Fair-trade organic and perfectly lovely, I found this at REI. Also available on their website for $10.
Birds on a Wire Photo Clips: Available at UrbanOutfitters.com for $10. I've also seen them at Blick. Comes with a 36" wire for stringing up your photos. The birds perch above each one.
Texts from Last Night Daily Calendar: This spit-take inducing calendar is available on Amazon for $11.69. Also findable in bookstores and some paper stores.
Pretty Polaroid Notecards: Available at UrbanOutfitters.com for $14.95; again, also available at Blick. Perfect for the nostalgic polaroid enthusiast on your list.
Letterpress Calendar: Paper Source has a gorgeous one for $18.50; it's the size of a CD case and props itself up on your desk.
Grassy Lawn Charging Station: Available on Amazon for $24.99. Plant yourself a bed of iPods.