A Summer Weekend on Cape Cod

Written By Maggie Varn

If you've never been to Cape Cod, you’re in for a treat. I just got back from a girls trip over Labor Day weekend—three nights of beach walks, ocean breezes, and amazing food. This was actually my third trip to the Cape, and it somehow gets better every time.

Where We Stayed

Over the years, I’ve stayed in Dennis Port, Chatham, and most recently Harwich Port. If I had to rank them, Chatham would be my first choice, and Harwich Port a close second.

This trip we stayed in a dream house in Harwich Port with a guest house on the property. Mornings and evenings were spent on the porch, coffee or wine in hand—it was perfect. The house was walking distance to both downtown Harwich Port and the beach, with Chatham just a short drive away. We already rebooked it for next Labor Day weekend we loved it so much!

Getting There

All of the girls flew into Boston Logan Friday morning. I arranged for the Chatham Bars Inn shuttle service to pick us up, and it was worth every penny. The drivers were on time, professional, and so friendly—it made transportation seamless the entire weekend.

Day 1: Arrival + Sunset Drinks

Settled into our Airbnb with spritzes on the back patio.

  1. Headed to The Ocean House in Dennis for beachside drinks and live music. The atmosphere was unbeatable—string lights and an ocean breeze.

Day 2: Chatham Day

  • Leisurely morning:

    • Some strolled the neighborhood admiring Cape Cod’s classic wood-paneled homes and hydrangeas.

    • Some grabbed coffee at Perks (tip: go early, it gets packed).

    • Others walked straight to the beach.

  • Picked up lunch at Mad Minnow and enjoyed it picnic-style on the sand.

  • Evening at Chatham Bars Inn:

    • Happy hour on the veranda (get the salted watermelon margarita—trust me).

    • Dinner at Salted Cod Tavern, the inn’s cozy indoor spot. Other dining options include the veranda (first-come), and the beachside grill (reservations open two weeks in advance).

  • Ended the night downtown at The Squire, a classic Chatham bar with live music.

Day 3: Beachcomber + Lobster Boil

  • Another relaxed morning before being shuttled to The Beachcomber in Wellfleet.

    • Think: a beachside cliff bar meets island vibes.

    • Painkillers + seafood = a perfect beach lunch.

  • Shuttle ride back (about a 45 minute ride).

  • Arrived home to the smell of dinner being prepped by Chef Heather from All Cape Personal Chef Service.

    • Menu: clams, whole lobsters (yes, we cracked them ourselves), potatoes, corn, homemade slaw, and fresh berry cobbler.

    • Eating this feast on the back patio was the most perfect ending to our trip.

Departure

On Monday morning, our trusty Chatham Bars Inn shuttle picked us up and dropped us off at Boston Logan. Easy, seamless, stress-free.

Bonus Recommendations (If You Have Extra Time)

If you have more than a long weekend, here are a few must-try spots in Chatham:

Final Thoughts

Cape Cod is one of those places that keeps pulling you back. With charming towns, ocean views, and incredible food, it’s the perfect girls’ weekend destination. After three trips, I can confidently say: I’ll be back again (and again).

Maggie Varn