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Link the Day — 2–3 Stops, One Parking Spot

The best grandkid days aren't one big thing — they're two or three smaller things that flow together. Here are our favorite multi-stop itineraries, each designed around a single parking spot.

The one-parking-spot rule

Each itinerary is built around a single parking spot (or a tight cluster). You move the car once — maybe twice — between an aquarium and an ice cream shop, not across three towns. The goal: a full, unhurried day that doesn't feel like logistics.

Norwalk, CT Year-round (aquarium) — best April–October for outdoor walks

A Morning in SoNo

Aquarium, waterfront ice cream, and a harbor walk — one parking lot.

⭐ Staff Pick
~3.5 hrs All walkable All ages

The itinerary

  1. 1
    Maritime Aquarium at Norwalk ~90min

    Sharks, harbor seals, jellyfish, and an IMAX theater. The aquarium is compact and well-paced — you won't feel rushed or like you're missing anything.

  2. 2
    SoNo waterfront walk ~20min

    A 5-minute walk from the aquarium takes you through the SoNo arts district and down to the waterfront. Let the grandkids lead — there's usually something interesting to stop and look at.

  3. 3
    Scoops & More (or Washington St ice cream) ~30min

    Several ice cream and treat options within 3 blocks of the aquarium. Washington St has the best density. Let the grandkids choose the shop.

  4. 4
    Stepping Stones Museum (rainy day backup) ~90min

    If the weather turns or you've got energy left, Stepping Stones is a 10-minute walk from the aquarium. Two big museums in one SoNo visit is a full day for young grandkids.

Parking: Park in the Maritime Aquarium lot on Water St — free with aquarium admission, and it covers the whole area.
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Westport, CT May–September

Westport Beach Day Done Right

Sherwood Island, a farm stand, and ice cream — all within 10 minutes of each other.

~4 hrs Short drives between stops All ages

The itinerary

  1. 1
    Sherwood Island State Park ~150min

    Connecticut's first state park has a wide sandy beach, fishing, and picnic pavilions. Easy walking, good shade at the pavilion. Ideal for 2–3 hours in the morning before the beach gets crowded.

  2. 2
    Gilbertie's Farm Stand, Westport ~30min

    A short drive from Sherwood Island, Gilbertie's is a working farm and nursery with a fantastic farm stand. Pick up lunch fixings, let the grandkids see the plants and herbs, and get something to bring home.

  3. 3
    Compo Beach Creamery (or local ice cream) ~30min

    Finish the day with ice cream near the beach. Several options on Post Rd in Westport. The walk from the car to ice cream is the perfect ending to a beach morning.

Parking: Park at Sherwood Island State Park. The lot near the main pavilion has the best access to the beach, picnic area, and facilities.
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Greenwich, CT May–October for beach; Bruce Museum year-round

The Greenwich Waterfront Loop

Greenwich Point, downtown ice cream, and the Bruce Museum — one town, three stops.

~4 hrs Short drives between stops All ages

The itinerary

  1. 1
    Greenwich Point Park (Tod's Point) ~120min

    A beautiful peninsula park with beach access, walking paths, and water views. Not as crowded as Sound Beach. Good for grandkids who want to explore as well as swim.

  2. 2
    Downtown Greenwich ice cream ~30min

    Greenwich Ave has several dessert options. Treat it as a palate cleanser between beach and museum — the walk down Greenwich Ave is part of the experience.

  3. 3
    Bruce Museum ~60min

    A small but well-curated natural history and fine arts museum. Good for 45–60 minutes — enough for younger grandkids without overwhelming. The rock and mineral collection is a perennial hit.

Parking: Start at Greenwich Point Park (Tod's Point) — parking requires a Greenwich permit in summer. Alternatively, park downtown and reverse the order.
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Stamford, CT Year-round (all indoor)

Stamford Rainy Day — No Sunshine Needed

Chelsea Piers skating, Stepping Stones, and downtown lunch. All indoors.

~4.5 hrs Short drives between stops Ages 3+

The itinerary

  1. 1
    Chelsea Piers Connecticut ~120min

    The ice skating rink is the centerpiece — it works for grandkids who have never skated and grandparents who have. Skate rental included. The massive facility also has rock climbing and gymnastics if the rink isn't the right fit.

  2. 2
    Downtown Stamford lunch ~60min

    The Mill River Park area has good lunch options. Easy to find something for mixed tastes. The park itself is worth a short walk through if it's not pouring.

  3. 3
    Stepping Stones Museum (Norwalk) ~90min

    If you want to keep going, Stepping Stones is 20 minutes from downtown Stamford and is the best hands-on museum in the region for under-10s. A full three-stop indoor day for ambitious grandparents.

Parking: Park in the Chelsea Piers garage (validated with admission). Everything else is a short drive; Stamford downtown parking is metered but easy on weekdays.
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Southbury, CT May–October

Southbury Family Fun Loop

Mini golf, farm creamery, and a lakeside park — easy parking, easy driving.

~3.5 hrs Short drives between stops All ages

The itinerary

  1. 1
    Gateway Fun Center ~90min

    Mini golf, go-karts, bumper boats, and an arcade. Start here when everyone has the most energy. The 18-hole course is manageable for grandkids of any age.

  2. 2
    Ferris Acres Creamery ~45min

    Farm-made ice cream in Newtown, 15 minutes from Gateway. Seasonal flavors, outdoor seating, and the actual farm visible behind the stand. The grandkids' reward for finishing the mini golf course.

  3. 3
    Kettletown State Park ~60min

    A quiet lakeside park with picnic areas, easy trails, and swimming in season. A good place to walk off the ice cream and let the grandkids run one more time before the drive home.

Parking: Each stop has its own parking — this loop works best by car. All three are within 15 minutes of each other along Route 6.
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Know a great multi-stop combo?

We're always looking for local favorites. If you've found a sequence of spots that flows perfectly from one parking lot, tell us.

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