Fall on Cape Cod: The Perfect Group Retreat

Three Days. Two Nights. Plenty of Time Together.

Gather your favorite people for a quintessential fall escape to Woods Hole. Whether it’s a weekend with girlfriends, a family gathering, a book club, a long-awaited reunion, a milestone birthday, or a small retreat, our 3-day, 2-night itinerary is designed to make the most of the season, with time to explore, linger over meals, wander the harbor, and simply enjoy being together.

Day 1 – Arrive & Gather

3:00 PM — Check-in at Woods Hole Inn
Settle into your rooms and meet in one of our many common areas with a warm fall welcome.

4:00 PM — Explore Woods Hole
Take a relaxed harbor walk and explore the village. For groups arriving earlier, add a stroll to Nobska Lighthouse

5:30 PM — Sunset Harbor Gathering
Gather for drinks and appetizers while enjoying the waterfront atmosphere at the Leeside Pub.

7:00 PM — Group Dinner
Enjoy dinner at one of Woods Hole’s many local restaurants. Keep the evening relaxed so guests have time to reconnect. We would be happy to provide recommendations like the Landfall Restaurant, Captain Kidd or Water Street Kitchen.

After dinner — Evening together
Return to the Inn for conversation, games, or a casual nightcap.

Day 2 – Explore Cape Cod

8:00–10:00 AM — Breakfast at the Inn
A leisurely breakfast gives everyone time to start the day together.

10:00 AM — Shining Sea Bikeway Adventure
Take a group ride or walk along the scenic trail. Fall is an ideal time to explore without the intensity of summer crowds.

12:30 PM — Lunch in Woods Hole
Give guests some flexibility to choose their own lunch or arrange a group meal. Locals Tip: Pie in the Sky or Quicks Hole Taqueria won’t disappoint!

2:00 PM — Choose Your Adventure

  • Check out a local brewery or winery
  • Browse local shops and galleries in Woods Hole or on Main Street in Falmouth
  • Take a fall nature walk around the historic Highfield Hall
  • Go on a cranberry bog tour
  • Hop on the ferry and take a Martha’s Vineyard day trip

6:00 PM — Return & Refresh

6:30 PM — Group Dinner + Celebration
Reserve a private or semi-private dinner where possible. This is a great opportunity for a birthday toast, reunion dinner, or group activity.

8:30 PM — “One More Round”
Check out the Leeside Pub next door for one more round of celebration.

Day 3 — Slow Cape Cod Morning

8:00–10:00 AM — Breakfast

10:00 AM — Final Woods Hole Walk
Take one last stroll around the harbor and waterfront.

10:30 AM — Group Photo
Capture the weekend together–on Nobska Beach with the iconic lighthouse as the backdrop perhaps.

11:00 AM — Check-out

It’s always sad to say goodbye, but you leave with lasting memories

Optional: Extend the day with lunch on Main Street Falmouth and check out the local shops on your way out of Falmouth.