Top 10: The Ultimate Cape Cod Summer Bucket List ☀️🐚 (2025)
Cape Cod is the ultimate summer destination, offering a perfect mix of natural beauty, outdoor adventure, and classic coastal charm. Whether you're a first-time visitor or a seasoned Cape Codder, there's always something new to experience. Make this summer unforgettable with these must-do Cape Cod adventures - Chatham’s Version! These are “Jenn and George approved” recommendations - Enjoy!
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1. Go Whale Watching 🐋
One of the most awe-inspiring experiences on Cape Cod is heading out on a whale-watching tour in Chatham. Departing from Cape Cod towns like Chatham and Provincetown, these excursions bring you up close to these majestic creatures. Don’t forget your camera for whale watching—you won’t want to miss capturing these gentle giants in action!
Check out these tour companies: Outermost Harbor Marine, Blue Water Entertainment, Down Cape Charters
2. Tour Iconic Lighthouses 🏠
Cape Cod lighthouses are some of the most picturesque lighthouses in New England. Explore the region’s rich maritime history by visiting iconic lighthouses such as Stage Harbor (my favorite), Chatham Lighthouse, and Nauset Light. Each offers stunning views and great photo opportunities for your Cape Cod lighthouse tour!
3. Indulge in a Traditional Cape Cod Clam Bake 🦞
No Cape Cod clam bake is complete without a classic New England lobster boil. Whether you join a local event or prepare one yourself on the beach or at your Chatham vacation rental, feasting on fresh lobster, clams, mussels, and corn on the cob is an essential Cape Cod experience. Pair it with a stunning seaside view for the perfect summer evening.
Our go-to’s for Lobster Clam Bakes:
Take Out or Cook In: Mac’s Chatham Seafood, Chatham Fish Pier
Eat In: Chatham Bars Inn Beach House. If you don’t want to cook and want to treat yourself this is a great option - reservations strongly recommended.
Check out our other local restaurant recommendations here.
4. Bike the Scenic Cape Cod Rail Trail 🚴♂️
Spanning over 25 miles and 6 Cape Cod towns, the Cape Cod Rail Trail takes you through picturesque towns, forests, and beaches. Rent a bike (or use ours!) and cruise from Dennis to Wellfleet, stopping along the way to explore charming villages and scenic Cape Cod overlooks.
5. Spend a Day at the Beach 🌊☀️
With over 500 miles of coastline, Cape Cod beaches boast some of the best in the country. Chatham beaches have many options for you to choose from, with 10 public beaches to explore! Our favorite is Pleasant Street Beach in Chatham, just down the street from Pleasant Chatham Cape - this small beach doesn’t have a lifeguard on duty but doesn’t require a beach sticker. Other favorites include Hardings and Lighthouse beaches. Check out the Chatham Chamber of Commercefor all the details on beach permits and fees.
6. Kayak or Paddleboard Through Serene Waterways 🚣
Explore Cape Cod waterways by kayak or paddleboard. Paddle through the peaceful waters of Pleasant Bay in Chatham, or venture into the marshes of Nauset Estuary for a scenic and wildlife-filled adventure. We love embarking from The Chatham Kayak Company at the end of Barn Hill in Chatham. If you time it right you can ride the tide out and take it back in without getting too exhausted from the effort! Don’t forget the sunscreen!
7. Watch the July 4th Parade in Chatham 🇺🇸
Chatham’s 4th of July Parade is one of the most beloved traditions on Cape Cod. Featuring festive floats, marching bands, and a patriotic spirit, this event is a must-see if you're visiting during the holiday. Pick a spot on the parade route and experience true Americana! We love to park ourselves at Pain d’Avignon on Crowell Road and get some delicious pastries and ice coffee while watching the parade.
8. Explore Charming Downtown Chatham 🛍️🍦
Downtown Chatham is the perfect place for a leisurely stroll. Browse local boutiques, grab an ice cream cone from Buffy’s Ice Cream, and enjoy the small-town Chatham charm. Don’t forget to stop by the Chatham Fish Pier to watch the fishing boats come in with the day’s catch. It’s a great spot to get up and close to the seals that call our town home.
Some of our favorite stops include:
- The Candy Manor: kids (and adults alike) love this spot for amazing fudge, penny candy and confections.
- Yellow Umbrella Bookstore: grab a beach read from a small, local bookseller.
- Sundancer's has great fashion finds and cute gifts to bring home.
- The Mayflower: if you love decor as much as I do, this is the store for you - so many unique coastal finds for the home, gifts for loved-ones, and games for the kids.
9. Catch a Cape Cod Baseball League Game ⚾
Experience America’s favorite pastime by attending a Cape Cod Baseball League game. This historic league has produced countless Major League Baseball stars. Cape Cod baseball games are free to attend, making them a fun and budget-friendly way to spend a summer evening. We personally route for the Chatham Anglers (obviously) and their home is at Veteran’s Field on Main Street (next to The Nun). Come for the game but stay for the popcorn!
10. Go on a seal tour
Chatham seal tours are a must-do! Chatham is home to thousands of harbor seals and gray seals during the summer. There are many spots to check them out including at the Chatham Fish Pier when the boats come in, along the shore, and at Monomoy National Wildlife Refuge. Our favorite thing to do is to take a boat tour to see and learn all about the Chatham seal community. There are a couple different options for tours but our go-to is Beachcomber Boat Tours at the Chatham Boat Company on Crowell Road.
Ready to Check These Off Your List?
Check out more family-friendly activities here
Make the most of your Cape Cod summer by staying in the heart of it all! Book your getaway with Pleasant Chatham Cape Properties for a perfect home base to explore everything the Cape has to offer. 🌊🏡
Cheers! xo,
Jenn + George