Beer and Brewing has a roundup of pairing suggestions from around the intertubes:
Suggestions from The Beer Chicks include these pairings:
Caramel DeLites (aka Samoas) with Maui Brewing Co.’s CoCoNut PorTeR
Tagalongs with Wells & Young’s Brewing Company’s Banana Bread Beer
Thin Mints with Kiuchi Brewery’s Hitachino Nest Beer Espresso Stout
Trefoils with North Coast Brewing Co.’s Old Rasputin Russian Imperial Stout
Central Track’s Melissa Mackaly suggests these pairings:
Samoas with Founders Brewing Co.’s Dirty Bastard
Thin Mints with Great Divide Brewing Co.’s Yeti Imperial Stout
Do-Si-Dos with Founders Brewing Co.’s Imperial Stout
Suggestions from the Brooklyn Brewshop include these pairings:
Thin Mints with Bootlegger’s Brewery’s Mint Chocolate Porter
Tagalongs with Brooklyn Brew Shop’s own Peanut Butter Porter
Dulce de Leches with Revolution Brewing’s Mad Cow Milk Stout
Lemonades with Brooklyn Brewery’s Sorachi Ace
And finally, Flying Dog Brewery includes the following pairings with its own beers:
Trefoils with Pearl Necklace Oyster Stout
Do-Si-Dos with Lucky SOB Irish Red Ale
Samoas with Raging Bitch Belgian-Style IPA
Tagalongs with Gonzo Imperial Porter
Thin Mints with Kujo Imperial Coffee Stout
And Wine Club Reviews and Ratings has these wine pairing suggestions:
By the way, Samoa fans, you can buy Samoa-flavored coffee creamer.
There are two types of Thin Mints made today, but both combine a wafer, chocolate, and peppermint flavoring. To truly experience the mint & chocolate combination, however, don’t reach for the milk – try a Syrah instead.
Samoas (Caramel deLites)
Banyuls is a red dessert wine from Southwestern France, which pairs amazingly with the dark chocolate stripes on Samoas. For a Plan B, pick up a Port.
Tagalongs (Peanut Butter Patties)
You’re going to see a trend here: when the cookie has chocolate, grab a bottle of red wine. Tagalongs are no different – find a fruity red wine such as Beaujolais or Zinfandel.
Light and refreshing, a Trefoil shortbread should be paired with Pinot Noir or even Sparkling wine if the mood is right.
When snacking on these shortbread cookies with lemon-flavored icing, grab a buttery Chardonnay like the 2009 Cambria Chardonnay from Uncorked Ventures.
My personal favorite: shortbread dipped in rich fudge. It’s a tough one, as it combines the light shortbread with the chocolatey fudge, but I’ll be enjoying mine with a Pinot Noir from Gold Medal Wine Club.
Chocolate Chip Shortbread
There is a lot of disagreement about what types of wine pair best with chocolate chip cookies in general. This one comes down to a matter of personal preference on white or red. You could either go with a dark Port or a sparkling white.
These are a lemon-based cookie similar to the Lemonades but covered with powered sugar. Try a Pinot Grigio/Gris.
Cranberry Citrus Crisps
Both sweet and tangy because of the cranberry, a good match for these would be a Viognier or the more popular Riesling.