Chatham

Day Trips

Make the most of your day with our curated plans, packed with Chatham's hidden gems and unique experiences!

day 1
Exploring Historic Center
morning
:

Start your day with a hearty breakfast at a local café, savoring freshly baked pastries and coffee. Afterward, take a leisurely stroll through the charming streets of Chatham, admiring the historic architecture and quaint shops. Don’t miss the Chatham Lighthouse, a picturesque spot to snap some photos and learn about the town's nautical history.

afternoon
:

Visit the Chatham Railroad Museum to dive deeper into the town's rich history and its connection to the railroad. Afterwards, enjoy lunch at a seafood restaurant, where you can sample the day's fresh catch while overlooking the scenic waterfront. Spend your afternoon browsing local art galleries and boutiques for unique souvenirs.

evening
:

As the sun begins to set, head to the Chatham Bars Inn for a cocktail with stunning ocean views. Enjoy a fine dining experience at one of the acclaimed restaurants in town, featuring local ingredients and a cozy atmosphere. Conclude your evening with a peaceful walk along the beach, taking in the sound of the waves and the crisp evening air.

day 2
Beach and Water Sports
morning
:

Kick off your adventure with breakfast at a beachside café, where you can enjoy the sound of the surf as you dine. Afterward, head to Chatham's famous beaches, like Hardings Beach, and choose a spot to soak up the sun or take a refreshing swim. For the more adventurous, rent paddleboards or kayaks to explore the coastline and nearby islands.

afternoon
:

Break for lunch at a beachfront shack, where you can relish delicious fish tacos or clam chowder. Spend your afternoon participating in water sports, such as jet skiing or windsurfing, and feel the thrill of the ocean waves. Don’t forget to take a break and relax on the soft sand, enjoying the beautiful surroundings.

evening
:

As the sun begins to set, return to your accommodation to freshen up and unwind. Head out for a casual dinner at a local pub known for its lively atmosphere and hearty fare. After dinner, take a sunset cruise to see the picturesque shoreline from a different perspective, with the sky painted in vibrant hues.

day 3
Nature and Wildlife Exploration
morning
:

Start your day with a light breakfast before venturing out to Monomoy National Wildlife Refuge. As you explore the refuge, keep your eyes peeled for various bird species, seals, and other wildlife native to the region. A guided tour can enhance your experience, providing insight into the diverse ecosystems found here.

afternoon
:

After a morning of exploration, enjoy a picnic lunch amidst nature, surrounded by the sights and sounds of the refuge. Spend your afternoon hiking the scenic trails, discovering hidden spots and taking in breathtaking views of the marshes and ocean. Consider bringing a camera to capture the stunning landscapes and wildlife you encounter.

evening
:

Return to Chatham in the evening and relax at your accommodation before heading out for dinner. Dine at a farm-to-table restaurant that highlights local produce, seafood, and wines. After your meal, take a stroll through the town center, soaking in the charming ambiance and perhaps stopping for ice cream on your way back.

day 4
Fishing Charter Adventure
morning
:

Wake up early and grab breakfast at a local diner, fueling up for a day at sea. Board a fishing charter that departs from Chatham Harbor, where you can learn from experienced guides about the best fishing spots and techniques. As you set out, enjoy the fresh ocean breeze and the stunning views of Cape Cod's coastline.

afternoon
:

Spend your afternoon reeling in fish while enjoying the camaraderie of fellow anglers on the boat. Whether you’re a novice or an expert, the thrill of catching a striped bass or bluefish will keep you engaged. When the charter returns, you’ll have the option to have your catch prepared at a local restaurant for dinner.

evening
:

After a day of fishing, unwind with a relaxing dinner at a seafood restaurant, where your fresh catch can be cooked to perfection. Savor the flavors of the ocean while enjoying the laid-back atmosphere of Chatham. Cap off your evening with a visit to a local bar or tavern, enjoying live music or casual conversation with the friendly locals.

day 5
Cycling the Cape Cod Rail Trail
morning
:

Start your day with a breakfast sandwich and coffee, then rent bicycles for a day of cycling fun. Head to the Cape Cod Rail Trail, a scenic path that stretches through beautiful landscapes, including forests, ponds, and quaint towns. Pedal along at your own pace, taking in the sights and sounds of nature.

afternoon
:

Stop for lunch at a charming café along the trail, enjoying local dishes and perhaps a cold drink to refresh you. After your break, continue your ride, exploring new sections of the trail and stopping to take pictures of picturesque views. Look for spots to rest and enjoy the surroundings, perhaps even spotting some wildlife.

evening
:

Return to Chatham and unwind at your accommodation, freshening up after an active day. Enjoy dinner at a local restaurant with a cozy atmosphere, where you can indulge in a hearty meal and share stories from your cycling adventure. After dinner, take a leisurely walk through town, appreciating the evening ambiance and local shops.

day 6
Cultural Heritage Tour
morning
:

Begin your day with breakfast at a historic inn, where you can appreciate the charming decor and rich history of the building. Afterward, visit the Atwood House Museum to learn about the early settlers of Chatham and view fascinating exhibits. Take your time to explore the museum grounds, which offer lovely gardens and views of the surrounding area.

afternoon
:

For lunch, choose a local eatery that reflects the town’s heritage, perhaps trying some traditional New England fare. Spend your afternoon visiting the Chatham Marconi Maritime Center, where you can discover the significance of radio communication in maritime history. Engage with interactive exhibits and enjoy the panoramic views from the center’s observation deck.

evening
:

As the day winds down, enjoy dinner at a restaurant that serves dishes inspired by local culinary traditions. Afterward, consider attending a performance or cultural event at a nearby venue, immersing yourself in the local arts scene. Conclude your evening with a nightcap at a cozy bar, reflecting on a day rich in history and culture.

day 7
Art and Craft Workshop
morning
:

Start your day with breakfast at a local café, fueling up for a day of creativity. Afterward, head to an art studio or community center offering workshops in painting, pottery, or crafts. Engage with local artists who will guide you through the process, allowing your artistic side to flourish.

afternoon
:

Break for lunch at a nearby bistro, where you can enjoy light fare and share ideas with fellow workshop participants. Continue your artistic journey in the afternoon, experimenting with different mediums and techniques while developing your own unique piece of art. Don’t hesitate to ask the instructors for tips to enhance your skills.

evening
:

After a fulfilling day of creation, return to your accommodation to relax and freshen up. Enjoy dinner at a charming restaurant that features works from local artists, creating a perfect ambiance for your evening. To wrap up your day, visit a local gallery to admire more artwork and perhaps purchase a piece to take home as a memory.

day 8
Historical Lighthouse Tour
morning
:

Start your day with breakfast at a local diner, enjoying the hearty meals that Chatham is known for. Afterward, visit the iconic Chatham Lighthouse, where you can explore the grounds and learn about its fascinating history. The view from the lighthouse is breathtaking, making it an ideal spot for photos.

afternoon
:

Enjoy lunch at a nearby seafood restaurant, experiencing the fresh flavors of the ocean. Afterward, join a guided tour that includes visits to other historic lighthouses in the area, learning about their significance and the role they played in maritime navigation. Each lighthouse has its own unique story and charm, providing insight into the region's rich maritime heritage.

evening
:

Wrap up your day with dinner at a coastal restaurant that offers stunning views of the water. Enjoy a leisurely meal while reminiscing about your lighthouse adventures. As night falls, take a moonlit walk along the beach, soaking in the tranquility of the ocean waves and the beauty of the stars above.

Discover Chatham

Read more in our Chatham 2025 Travel Guide.

Chatham Travel Guide