After our stay in Boston, Andrew, baby O and I drove out to Rockport for a few days at the shore. Andrew used to visit Cape Ann as a kid, so coming back to this area was a nostalgic trip down memory lane for him.
Where we stayed: We rented a home right in historic Bearskin Neck at the heart of Rockport. This two-bedroom cottage has views of the ocean from the second floor and roof deck. The open concept downstairs was pretty child-friendly and included a metal coffee table that baby O deemed the best drum he had ever encountered. Baby O’s room had 3 single beds, so this house would be great for larger families as well. Our favorite feature was the roof deck with grill, where we cooked steaks and lobster one night after baby O was asleep.
What we did: We definitely took things slow in Rockport. As we arrived a bit early in the season and were visiting during the week rather than on a weekend, some restaurants and shops were not yet open. Here’s what we enjoyed most:
Bearskin Neck, Rockport: A great place to shop and stroll. Andrew had lots of happy memories here. We strolled down to the jetty and hopped out onto the rocks. We popped in the Country Store to show baby O the player piano (best thing he’s ever experienced) and stopped by the Pewter Shop for an ornament to commemorate our trip (I buy an ornament on every trip we take). We snapped photos of Motif #1, a lobster shack so named as it has been the subject of paintings and photography since 1840. We strolled around the bay to the Headlands for lovely views back over Rockport, and even had a family portrait session with Esther Mathieu on Old Orchard Beach.
Halibut State Park: Our favorite spot in the area and well worth a visit. The loop around the quarry is completely stroller accessible and gorgeous. We took along baby O’s Ergobaby carrier to go off-road if needed, and hiked down to the shoreline with that. There are picnic tables, making this a great lunch spot as well.
What we ate:
Roy Moore’s: The full-service restaurant wasn’t open for the season yet (a handwritten sign said they would open in June), but the lobster shack was. You can take out or eat on their back deck. Baby O tried his first lobster here (smashing success).
Helmut’s Strudel: The namesake strudel with homemade vanilla ice cream is well worth a stop.
Caitlin Kenney Smith 
Rockport looks stunning!
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