Dive into Boston’s best pies
Satisfy your sweet tooth with a visit to Rosebud American Kitchen & Bar right in Davis Square. This re-invented diner serves up delicious brunch, dinner and, of course, its world famous pies. Take your pick from slices of Cookie Dough Brownie, Banana Bourbon Cream, or Peanut Butter Fudge -- or treat yourself and your date to one of everything.
Ice skating at Frog Pond
What better way to bond with someone than to take a couple laps around an ice rink hand-in-hand. Yes, the potential of falling is inevitable but make sure you’re geared up appropriately for the evening. With the snow (sadly) creeping its way into the forecast, this is a go-to for quality romance and trust building.
Explore the many shops and food stops in Union Market
A quaint courtyard in the heart of Union Square, Bow Market has just about everything you need for a fulfilling first date -- small bites, a brewery, live music, wine and more. If you’re looking for a special event (and to save some cash), on Saturday, November 9, Bow Market’s ringing in its 1 year anniversary, with food and shopping specials from 12pm - 8pm.