This area is the heart of Connecticut’s so-called “Gold Coast,” a name that presumably refers to more than just the color of the leaves in fall. Westport is the community that Ricky and Lucy moved to in I Love Lucy and where Martha Stewart lived for 25 years. It’s a largely residential community of quiet cul-de-sacs and giant trophy houses.

Next up, the maritime city of Norwalk is still very much tied to its past. Its long history is best embodied along the Norwalk River in the redeveloped and trendy South Norwalk neighborhood (which has been cheekily rebranded SoNo). That’s the place for shopping excursions, excellent dinners, and late-night dancing.

By contrast, Stamford is all business—large corporations are headquartered here, and have modernized seemingly every inch of the metropolis. Most of the tourist attractions lie in the northern area of the city, where the bulk of shops, restaurants, museums, and entertainment can be found.