A Weekend in Connecticut Itinerary

At the end of May, Jay is going on a quick work trip to Connecticut so baby Connor and I are planning to tag along. We’re hoping this will be the first of many mini vacations we take with Connor! A short weekend in Connecticut seems like a perfect place to start. Thankfully its driving distance so we don’t need to worry about flights. Here’s a quick peek into where we’ll stay and things to do in the area.

Where to Stay

Bridgeport Area – Jay’s conference is in Bridgeport so we’re spending two nights nearby. At SpringHill Suites you earn double the Marriott points compared to Residence Inns but still get a free breakfast! Plus, we’ll have more room to spread out in their larger hotel suites.

SpringHill Suites Milford – 50 Rowe Ave, Milford, CT 06460

New Haven Area – I decided to spend our third night a bit further up the coast. New Haven is host to Yale University and there are a bunch of cute coastal towns a short distance away.

Holiday Inn Express Branford – 309 E Main St, Branford, CT 06405


What to Do

With an infant in tow, we’re obviously limited on what we’ll be able to see and do during our weekend in Connecticut. However, here’s a list of options for both the Bridgeport and New Haven areas.


  • Visit the Seaside – If it’s nice out we’ll take the stroller to Captain’s Cove boardwalk or Seaside Park for a walk along the water.
  • Pequonnock River Trail – This trail runs for 16 miles along the scenic Pequonnock River. It sounds quite a bit more pleasant than our usual walks through our neighborhood.
  • Walnut Beach Creamery – Obviously I had to look up a local ice cream shop! This gourmet ice cream parlor with unique homemade flavors is luckily just 2 miles from our hotel 🙂
  • Beardsley Zoo – The only zoo in Connecticut contains exhibits featuring monkeys, tigers, snakes, birds, bison, and many more.
  • Discovery Museum and Planetarium – If Connor was a bit older, we would definitely visit this
  • The Barnum Museum – P.T. Barnum lived in Bridgeport for 40 years (and was even the mayor at one point)! This museum is dedicated to his life and work with the circus.

New Haven & Beyond

  • Yale University – Both self-guided audio tours and student led tours of the university are available! I’d love to do the student led in depth tour, but with a baby in tow we’ll see how much we manage with just the audio version.
  • East Rock Park – This vantage point offers sweeping views of New Haven from a higher elevation.
  • Old Saybrook – A short drive up the coast leads to Old Saybrook, one of the oldest New England towns. It’s full of charm and features a downtown located right along the waterfront.
  • Hammonasset Beach State Park – 2 mile long beach with a boardwalk. Perfect for taking a stroller!



  1. Hope you have a wonderful little trip! We are also not far from Connecticut, so thank you very much for the ideas for a quick getaway.

  2. There is a nice used bookshop in Niantic CT. It is probably about an hour from New Haven. It is called The Book Barn. 🙂

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