We went to the Cape the last week of September, and really lucked out with the weather. When we arrived it was chilly and we got a taste of fall (and I got to break out the fall fashion) but then it got warm and we had summer-like weather to finish out our trip. I had been looking at some of the local resorts, but we ended up renting a house after finding this rental company that just rents Cape houses and comes highly recommended. I was nervous about renting. I won’t do Airbnb/VRBO after some bad experiences, but this was a really great experience and we’ll definitely use them again when we return to the Cape.
As promised, I have rounded up my Cape Cod recs. It’s definitely a magical place for a family. There’s something about the shingled cottages, salt air, and slower pace that instantly makes you want to kick off your sandals and stay awhile. Whether you’re heading for a long weekend or planning your family’s annual getaway, here’s everything I’d recommend — from where to stay and eat to the best beaches and activities for kids.
Where to Stay
I spent a lot of time research each town to figure out the best place for us to stay. As we discovered, each town has its own magic so I honestly don’t think you can go wrong but it depends on what you’re looking for. One thing to keep in mind is that some of the towns are nearly an hour apart — the Cape is huge, so if you have friends in a certain area, you may want to keep that in mind when booking where you stay. We stayed in Chatham but I’ll share a little about the other places too.
- Chatham: We decided to stay in Chatham as it felt like it would be the liveliest during the shoulder season, is where some of the resorts we had been considering are located and has that quintessential Cape feel — think hydrangea-lined streets, chic boutiques, and an old-fashioned main street. We had been considering visiting Chatham Bars Inn for a long time and I still want to go back and stay there — it’s right on the beach, supposedly amazing for kids from friends who go every year (they have a kids’ club and pool), and walking distance to town. (For something more low-key, my friends also recommended The Chatham Wayside Inn.) We found that Chatham had it all — the beaches, great houses to rent but also great resort options, lots of restaurants and plenty of things to do in town.
- Wellfleet: This area was probably our runner up. Cahoon Hollow Beach is a great spot to hang with the fam and they had lots of great house rentals in the area.
- Falmouth: This was another area we considered. It’s perfect for younger kids — lots of calm beaches, bike paths, and easy access to the ferry for a day trip to Martha’s Vineyard. Sea Crest Beach Hotel is family-friendly with direct beach access that people love. We drove there one morning, and it’s a hike from Chatham so just something to keep in mind if you like the idea of spending time there or taking the ferry.
Del Mar Vacations has rentals all over the Cape, so you can filter by what you need from a house and the area you want to stay in.
Where to Eat
Dining with kids on the Cape was surprisingly easy — most restaurants are really casual, and many are walk-up spots with picnic tables and ocean views. Granted we were there in the shoulder season, but I felt like even when it’s busy, nothing felt as fancy or exclusive as in some of the other neighboring vacation destinations like the Cape and Nantucket. As promised, I rounded up all recs we received.
- The Squire (Chatham): Classic Cape vibes and a must for fried clams.
- Sesuit Harbor Café (Dennis): Picnic tables right on the water — grab lobster rolls and watch the boats go by.
- Arnold’s Lobster & Clam Bar (Eastham): Great for kids — there’s mini golf next door, and it’s all very low-stress.
- Mac’s Shack (Wellfleet): A little more elevated but still family-friendly. Fresh sushi, oysters, and amazing cocktails.
- Café Chew (Sandwich): Perfect for breakfast or lunch on your way onto (or off) the Cape.
- Filling Station
- The Airport for breakfast
- Chatham Perk for sandwiches
- Blue Fin in Chatham for sushi
- Spinnaker in Brewster for dinner
- Winslow’s Tavern in Wellfeet for date night
- Fisherman’s View on Canal in Sandwich
- Captain Parker’s
- Pizza Barbone
- Anejo
- The Black Cat
- Mary’s Fish 2
- Del Mar Chatham for early family dinner
We could walk in anywhere when we went, but in summer, I’ve heard the waits are long so make reservations well in advance when you can.
Best Beaches for Kids
- Ridgevale Beach (Chatham): Calm tide pools that little ones can safely explore.
- Mayflower Beach (Dennis): At low tide, the sandbars stretch forever — it’s like nature’s water park.
- Old Silver Beach (Falmouth): Clear, warm water and gentle waves.
- First Encounter Beach (Eastham): Gorgeous sunsets and perfect for evening
Things to Do with Kids
- Bike the Cape Cod Rail Trail: Rent bikes and cruise the path that runs from Dennis to Wellfleet.
- Chatham Fish Pier: The kids love watched the boats unload their catch — it’s surprisingly entertaining.
- Catch a Cape Cod Baseball League Game: This is a favorite of our friends who go every summer and is free to go.
- Mini Golf: There are so many places to go. Our friends recommended Pirate’s Cove, which was fun.
- Whale Watch Excursion from Provincetown: It was too windy when we went, but it sounded like such a fun activity.
- Barnstable County Fair
- Cape Cod Children’s Museum
- Cape Cod Maritime Museum
- Cape Cod Toy Library
- Cape Cod Inflatable Park
- Wicked Waves Water Park
- Take the Ferry to Martha’s Vineyard or Nantucket
- Nickerson State Park: Great for hiking, kayaking, and picnicking around the ponds.
The beaches are so beautiful, it was also fun to just do nothing but hang out on the beach and go back home to cook dinner and watch movies.
I’m sure there’s lots I’m missing. We only had a few days there and there’s so much to explore and do. And of course even more in summer.
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