Meet Halfway in Stratford, Connecticut

Aug 18, 2025

Stratford shoreline with lighthouse, seawall, and Long Island Sound

Splitting the distance between Philadelphia and Boston lands you in a sweet spot on the Connecticut shoreline: Stratford. I love it because it keeps meetups simple—easy off I-95, a walkable beach-and-river scene, and enough low-key attractions that you can park once and let the day unfold. If your group wants breezy views, a little history, and options for coffee, lunch, or a casual pint, Stratford makes the middle feel like a destination.

Great halfway spots in Stratford

Short Beach & Lordship Seawall — My go-to first stop for salt air and an easy stroll. Short Beach sits where the Housatonic River meets Long Island Sound, with a flat walkway and broad views; the Lordship Seawall a few minutes away is perfect for sunset and boat-watching. Bring a light jacket—there’s usually a breeze down here.
Stratford Point Lighthouse — A classic cast-iron tower guarding the mouth of the Housatonic since the 1800s. Even a quick look is worth it if you’re already in Lordship; the point has that “edge-of-the-map” feel that makes a meetup memorable.
Great Meadows Marsh (McKinney NWR) — When we want a nature reset, we loop the restored salt-marsh paths for birdwatching and big-sky photos. It’s a reminder that the coastline here is still wild in the best way.
Boothe Memorial Park & Museum — A quirky, green hilltop campus overlooking the Housatonic with historic buildings and gardens. It’s peaceful and photogenic—great for a midday walk-and-talk.
Two Roads Brewing / Area Two — If your crew is into craft beer, cap the day with a flight. Spacious taprooms, indoor/outdoor seating, and an easygoing vibe make it an effortless meetup finale.
Roosevelt Forest — Prefer trees to tide? This 400-acre town forest has mellow trails for a quick hour in the woods before heading home.

Quick meet plans

Choose “Philadelphia” and “Boston” on the homepage, then select Stratford, CT as your midpoint.
Arriving by car: Hop off I-95 (Exit 30–32 range works well). Park once near Short Beach or in Lordship for coast time; or head to Boothe Park for a quieter green start.
Arriving by rail: Meet at Stratford Station on the Metro-North New Haven Line, then rideshare 10–15 minutes to the beach or lighthouse area.
2–3 hour plan: Seawall stroll → Short Beach walk → café or casual lunch.
Half-day plan: Morning at Boothe Park → marsh walk at Great Meadows → late-afternoon lighthouse stop → tastings at Two Roads before the drive back.
Pro tip: Coastal wind picks up—hat and light layer help. If someone’s running late, the brewery or the park are easy places to linger.

Stratford’s charm is how effortless it makes a halfway day: water, walks, one or two simple attractions, and you’re never more than a few minutes from coffee or a table to keep the conversation going. Between Philly and Boston, it’s the kind of middle ground you’ll want to revisit.