30 Activities I Plan on Checking Off My Summer Bucket List

30 Activities I Plan on Checking Off My Summer Bucket List

30 Activities I Plan on Checking Off My Summer Bucket List

A few years ago when I was living in Los Angeles, I made a summer bucket list which was filled with 25 things I wanted to do before the season ended. It had activities that could only be done in L.A., that were mixed with typical fun stuff like having a bonfire on the beach and making s’mores. As that September approached I checked off mostly everything on my list, which made for a remarkable three months.

This year will be my first full summer on the East Coast in almost 10 years. (In 2020, I spent the end of August here, but so much was closed because of Covid restrictions.) Since I’m making up for years of being away, I curated a summer bucket list in hopes of checking everything off before autumn approaches. Rather than mix New York City and Connecticut related activities, I’m going to keep this one strictly for when I’m at my parents’ beach house in CT. Some of the items I’ve listed are a bit of nostalgia since they were things I enjoyed as a child. Others I haven’t experienced yet, like trying new restaurants, going on day trips, and exploring unique shopping areas. Here are 30 things I can’t wait to do before Labor Day.

P.S. I started composing this list in the beginning of June and I’ve already accomplished a few things on it. If there’s a *star next to the item, it means it’s been checked off.

1. Go miniature golfing and then have dinner by the marina.

2. Have a family game night with 1980s and 1990s trivia.

3. Find an intriguing book to read on the beach.* (Just finished Good Girls on Bad Drugs which was on my summer shopping list.)

4. Visit the boho/music/oddities store Old Glory which was a favorite of mine during my teen years.

5. Walk the charming streets of Madison, CT and stop in RJ Julia Bookstore, Ciao Bella, Robertson Madison, and J.Horton.

6. Take a ferry to Thimble Islands and spend the day exploring the area.

7. Watch fireworks over Long Island Sound.* (They were a-m-a-z-i-n-g! You can read about my July 4th here.)

8. Cool off with a Pina Colada from the Sunset Bar and Grill after spending a hot day on the beach. 

9. Get ice cream from Daisy’s ice cream truck.

10. Try a new restaurant like The Copper Beech Inn, The Ancient Mariner, or The Blue Oar.

11. Collect seashells, stones, and sea glass to make jewelry this fall.

12. Have breakfast at The Tea Kettle and order s’mores, blueberry lemon poppy, or strawberry shortcake pancakes. 

13. Spend a Sunday thrift shopping. Mine (Mystic) and Cinderella’s Attic (Guilford) are both highly recommended. 

14. Listen to live music—it doesn’t matter where or what kind because it’s been way too long! 

15. Have dinner at Bill’s Seafood while watching the sunset. 

16. Get my boating license.

17. Order pie from Oyster River Market.* (Had my favorite—key lime—for July 4th.)

18. Visit a local farmers’ market for fresh produce and baked goods. Here are a few I’d like to check out—Chester Sunday Market, Bishop’s Orchards Market & Winery, and Rose Orchards

19. Take the ferry to Block Island, RI for a day of shopping, sightseeing, and dining out. (Enjoy a Del’s Frozen Lemonade and an Oreo cookie like I did in 2019.) 

20. Revamp my beach playlist.

21. Walk around Olde Mistick Village and visit the old fashioned general store.*

22. Make s’mores at night and under the stars.* (Already did this but will again many times this summer.)

23. Take the ferry from New London, CT to Montauk Village, NY and spend the day exploring the area.

24. Go for plenty of beach jogs and stop to photograph the coast and the flowers. 

25. Attend the New England Taco Festival on July 31st.

26. Have lunch or dinner at the Griswold Inn and then walk around Essex.

27. Stop by Madison Cheese and pick up ingredients to prepare a charcuterie board. 

28. Enjoy the award-winning Sunday brunch at Water’s Edge Resort & Spa just like I did growing up.

29. Go on a pizza crawl in New Haven and discover the best tasting pie. 

30. Create a cocktail so that every time I drink it, it will bring back memories of the summer of 2021.

If you live in New York City, you can take the Northeast Regional train from Penn Station to Old Saybrook. It takes a little over 2 hours and once you arrive you’ll be in close proximity to a ton places mentioned in this post.

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