Feel the thrill as you embark on a journey through multiple editions of our signature activity—Chatham Scavenger Hunt—uncovering iconic landmarks, lively plazas, hidden murals, and tucked-away treasures unique to this Atlantic getaway.
Gather your group for trivia quests that test your wits, photo challenges that capture laughter, and creative puzzles—all tracked by our sleek app so you can compete for points and celebrate victories together!
Top Outdoor Activities In Chatham, Massachusetts
Step into the sun-drenched streets of Chatham, where Cape Cod Charm meets adventure around every corner. Whether you are drawn to the historic seaport or captivated by Monomoy Island's breezy shores, Outdoor Activities in Chatham promise unforgettable memories for locals and visitors alike. Experience the town's vibrant spirit as you uncover must-see sights and hidden gems on your next day trip. Discover why Outdoor Activities are the ultimate way to view Chatham from a fresh perspective.
Adventurers exploring in Chatham & Around The World!
Outdoor Experiences in Chatham, Massachusetts
Get ready to experience our expertly curated list of Outdoor Activities in Chatham, each designed to spark curiosity and excitement. These unique adventures invite you to explore iconic landmarks, colorful neighborhoods, and local secrets while engaging your sense of fun. Every activity is crafted for families, friends, or solo explorers looking for something truly memorable. Dive into these top experiences and let your adventurous side lead the way through Chatham's most recommended outdoor activities.
More Hunts Nearby
Can't find what you're looking for in Chatham? Check out these great scavenger hunts within 30 miles.
16.7 mi away
5.0 (25 reviews)
Barnstable Scavenger Hunt Scavenger Hunt
Downtown, Hyannis, Massachusetts
Ahoy, mateys! Set sail on a scavenger hunt through Hyannis Port, Barnstable‘s hidden...
17.8 mi away
5.0 (20 reviews)
Barnstable Bounty Bonanza Scavenger Hunt
Downtown, Barnstable Town, Massachusetts
Embark on a scavenger hunt through Barnstable Town‘s Downtown, uncovering historic gems...
28.1 mi away
5.0 (23 reviews)
Provincetown: Whispers in the Fog
Downtown, Provincetown, Massachusetts
Explore Provincetown's downtown on a self-guided, app-led ghost tour packed with riddles,...
28.1 mi away
4.9 (12 reviews)
Fun and Adventure Sandwiched! Scavenger Hunt
Downtown, Sandwich, Massachusetts
Sandwich is filled with history and charm! Let us guide you through a thrilling scavenger...
28.2 mi away
4.9 (14 reviews)
The Crown Jewel of Cape Cod Scavenger Hunt
Downtown Waterfront, Provincetown, Massachusetts
The crown jewel of Cape Cod is Provincetown. We'll help you navigate these tight historic...
28.3 mi away
4.9 (15 reviews)
Nantucket scavenger hunt
Downtown, Nantucket, Massachusetts
Whale, hello there! Dive into Nantucket‘s downtown scavenger hunt, unveiling maritime...
29.1 mi away
5.0 (20 reviews)
Boo on the Dunes
Downtown, Nantucket, Massachusetts
Experience a self-guided downtown ghost hunt tour in Nantucket with app-led clues,...
An Epic Chatham, Massachusetts experience
How Our Chatham, Massachusetts Outdoor Activities Work
Our experts have researched over 3,050 cities—including more than 50 across the Northeast—to craft unforgettable Outdoor Activities tailored just for you in each location. Every experience features clear instructions, custom routes highlighting must-sees plus quirky trivia quizzes inspired by real discoveries from our team. During each adventure around town, participants explore entirely on foot: answering trivia at historical markers, snapping photos at colorful murals or public art installations, solving clever puzzles—and racking up points through our award-winning app as they compete with others enjoying Outdoor Activities across all of Chatham.
1
2
3
Top Outdoor Attractions In Chatham
Chatham brims with top attractions perfect for outdoor enthusiasts eager to soak up coastal beauty and rich history. Stroll past classic lighthouses, bustling harbors, art galleries filled with regional masterpieces, and inviting green spaces alive with local energy. From live music on Main Street to sweeping Atlantic views at Lighthouse Beach, every stop offers a new way to enjoy sightseeing in this charming Massachusetts town. Click on each location to see related activities.
1
Chatham Civil War Monument
Visit Chatham's Civil War Monument at Main and Seaview. Locals say it faces sunrise to honor new beginnings. It's a unique outdoor spot to reflect on history while sightseeing in Chatham.
2
Chatham School Clock
See Main Street's School Clock, a legendary icon since the early 1900s. It's hands once froze during a huge blizzard—true Cape Cod resilience! A unique sight on your day trip to Chatham.
3
Oyster Pond Beach
Relax at Oyster Pond Beach, where calm waters meet soft sands—a perfect summer retreat. Sometimes glowing with bioluminescence, it's an Atlantic adventure not to miss in Chatham.
4
World War I Memorial
Pause at the Eagle Monument overlooking Chatham's Historic Harbor Hub. Locals whisper that it watches over the town eternally—a must-see for first-time visitors exploring local lore.
5
Chatham Windmill
Feel history come alive at Chatham Windmill—the oldest working landmark here. On breezy days, it's sails hum like a Cape Cod lullaby—a unique experience when visiting this lighthouse town.
6
Little Free Library
Visit Nautical Nook Library Box—a charming community hub where locals swap stories after summer festivals. This hidden gem is perfect for book lovers seeking unique things to do in town.
7
Eldredge Public Library
Explore Eldredge Public Library with it's arched windows and secret garden nooks—a Cranberry Coast icon rich with history and charm ideal for an afternoon escape.
See our Top Outdoor Activities By Neighborhood
Discover how Outdoor Activities bring out the best in Chatham's beloved neighborhoods—from Old Village Stroll's historic homes to Oyster Haven's waterfront delights and beyond. Each area reveals it's own character when explored outdoors—click on these neighborhoods to see the related activity.
12,000+ Reviews For our Hunts
See what people say about our outdoor activities in Chatham
Locals and visitors rave about our Outdoor Activities in Chatham! With glowing five-star reviews like 'The best day we spent in Cape Cod!' guests trust us for fun-filled outings that showcase everything special about this city. See why so many recommend our experiences when visiting Chatham.
This experience was perfect for tourists like us. We got to see iconic spots and learn about their significance along the way.
Chris T.
Such an enjoyable walking tour! We uncovered hidden gems in downtown, making it one of the best things to do in Chatham.
Anna M.
The Chatham School Clock was fascinating! A great thing to do while wandering through this charming neighborhood.
Kevin W.
We loved using ScavengerHunt.com for this interactive experience. It made exploring downtown so much more engaging and fun!
Laura M.
FAQs.
What are some fun Outdoor Activities in Chatham?
Are scavenger hunts good for groups in Chatham?
I am new to Chatham what do you recommend?
I am a Chatham local would this be fun for me?
What is the full list of all the scavenger hunts and activities that I can do in Chatham
LOCAL INSIGHTS
Fun Chatham Facts and Hidden Gems
Did you know that Chatham was settled in 1664 as a humble fishing village before blossoming into today’s celebrated Summer Retreat? It's storied past includes centuries-old cranberry bogs and legendary shipwreck tales along rugged Atlantic shores.
The town’s famous lighthouse has been guiding sailors since 1808—and even now seals gather near—
The town’s famous lighthouse has been guiding sailors since 1808—and even now seals gather near—
© 2016-2025 Let's Roam, LLC. Let’s Roam® is a registered trademark. All Rights Reserved.
✕
Holiday Flash Sale: Up to 55% off all tickets and passes
Hey! Sorry to interrupt.
We’re Charlie and Mike, founders of ScavengerHunt.com
Want an extra 10% Off Your Order?
NO, CONTINUE SHOPPING
Unlock your extra 10% off your first order!
Final step to get your extra 10% off!
Sign up for email & texts to get your code
MAYBE LATER
