Your Cape Get Away

A Cozy 3-Day Fall/Winter Getaway in Chatham, Cape Cod (2025)

November 2024

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Are you ready for a fall or winter escape to the charming seaside town of Chatham on Cape Cod? Our 3-day itinerary is perfect for those looking to enjoy the quiet beauty of the Cape, indulge in fresh seafood, explore local shops, and unwind in one of our cozy vacation homes. Whether you're planning a short weekend trip or a mid-week retreat, Chatham offers an unforgettable experience during the off-season.

Day 1: Arrival & Exploration in Chatham

Morning: Start your Cape Cod getaway by arriving at one of our Pleasant Chatham Cape Properties, where comfort and Cape Cod charm await. After settling in, head over to Pain D’Avignon for a delicious breakfast, complete with fresh coffee and homemade french pastries. It’s the perfect way to fuel up for the day ahead.

Late Morning: Take a stroll along Main Street Chatham, where you'll find charming boutique shops and local businesses. Don’t forget to pick up some Cape Cod-inspired gifts and souvenirs to take home!

Lunch: Enjoy a leisurely lunch at The Impudent Oyster, a favorite for fresh Cape Cod seafood in a warm, welcoming atmosphere. Try the clam chowder or lobster roll—both are must-haves!

Afternoon: After lunch, take a relaxing walk along Chatham Lighthouse Beach. The crisp fall or winter air and scenic ocean views make this a peaceful spot to enjoy the natural beauty of Cape Cod's coastline. If you are adventurous you can walk down to check out the Occupy Chatham Beach Shack.

Late Afternoon: Head over to the Chatham Fish Pier for some seal watching. Even though the Fish Pier Market closes for the season on November 3, you may still catch seals looking for food. It’s a quintessential Cape Cod experience!

Evening: For dinner, treat yourself to Bluefins Sushi & Sake Bar. This popular spot is known for its creative sushi dishes, fresh seafood, and cozy ambiance—ideal for a relaxed evening out in Chatham.

Night: After dinner, return to your vacation home for a cozy night in. Whether it’s by the fireplace or outside under the stars by the fire-pit, our properties offer the perfect setting to unwind and relax after a day of exploring Chatham.

Day 2: Cape Cod Adventures & Relaxation

Morning: Start your second day with breakfast at Hangar B Eatery, a local gem located at the Chatham Airport. Known for its delicious brunch options and homemade donuts, it’s the perfect start to another day of exploring.

Mid-Morning: Next, head over to Monomoy National Wildlife Refuge for a peaceful nature walk. This protected area offers stunning views, birdwatching opportunities, and a serene escape from the hustle and bustle.

We met a friend on our way to Monomoy Refuge

Lunch: For lunch, visit The Chatham Squire, a local favorite - where you can enjoy comfort food with seasonal ingredients, all while soaking in the cozy atmosphere of Chatham.

Afternoon: Spend the afternoon exploring local art galleries or catching a movie at the historic Chatham Orpheum Theater.

Evening: End your day with a delicious dinner at Chatham Wine Bar, where you can savor an exquisite farm-to-table menu and sip on locally sourced wines. It’s the perfect way to wrap up your Cape Cod adventure.

Day 3: Local Treasures & Relaxation

Morning: On your final day, take a peaceful morning walk along Pleasant Street Beach, just minutes from Pleasant Chatham Cape. Even in the fall and winter, the beaches offer serene views and a calming atmosphere.

Mid-Morning: For brunch, stop at Chatham Perk, a local gem known for its laid-back vibe and comforting breakfast options.

Afternoon: If you’re a fan of learning more about the local ecosystem, pay a visit to the Chatham Shark Center. Their interactive exhibits and fascinating information about Cape Cod’s great white shark population will definitely leave an impression. It’s a unique experience that’s both educational and fun.

What should you bring with you on your trip to Chatham in the Winter?

The weather can fluctuate in the Winter so double check that forecast before you leave - and be specific in searching Chatham's weather as it is common for several degree differences on Cape than the mainland. In any event, you can't go wrong bringing the following items:

Winter coat or parka
Winter boots for walking - weatherproof for the beach
Wool socks to keep your feet warm and dry
A warm hat and gloves
A digital camera to capture all your memories

Plan Your Cape Cod Escape with Pleasant Chatham Cape Properties

From seal watching and beach strolls to cozy dinners and exploring Chatham’s local charm, our 3-day itinerary gives you a taste of everything Chatham has to offer in the off-season. Whether you're visiting for a quiet retreat or a fun-filled weekend, Pleasant Chatham Cape Properties is the perfect place to stay. Book your getaway now for an unforgettable Cape Cod experience!

Cheers!

xo,

Jenn + George