Chatham Wayside Inn

Name: Chatham Wayside Inn
Address: 512 Main Street, Chatham, MA, 02633, US
Telephone: +15089455550
Price range: $$$

Home
United States
Chatham, MA
Chatham Wayside Inn

Call Directions Website Contact the business

Set in the heart of the picturesque seaside village of Chatham, Cape Cod, the Chatham Wayside Inn of

Located on the "elbow" of Cape Cod, Chatham is surrounded on three sides by water -- Pleasant Bay, Nantucket Sound, and the Atlantic Ocean. Chatham benefits from Mother Nature's "natural air conditioning" with comfortable summers, exquisite autumns, and mild winters. Beaches, golf, shopping, antiquing, walking, birding, biking, fishing, kayaking, lighthouses, seafood, history, salt air, windmills... this is what makes Cape Cod so special. Chatham has carefully and beautifully preserved the flavor of a small New England town with great style and charm, creating an ideal destination to experience that "stepping back in time, olde Cape Cod" feeling.

10/30/2026

🎄🥂 Christmas magic, New Year's sparkle, and a little Cape Cod charm! Celebrate the holidays in downtown Chatham with a festive stay at Chatham Wayside Inn and two unforgettable events right downstairs at Wild Goose Tavern!

🦞 Christmas Eve Feast with Friends | December 24
Gather your favorite people for an all-day seafood feast filled with holiday cheer, delicious food, and a special $10 kids menu for ages 10 and under.

🔮 New Year's Eve: The Fortune Teller's Ball | December 31
Your future looks festive! Ring in 2027 with a fabulous buffet, cocktails, street magicians, tarot card readings, live music, and a midnight countdown. Plus, late-night fries and sliders to keep the celebration going!

🛏️ Make a night of it! Our exclusive New Year's Eve Overnight Package includes your accommodations at Chatham Wayside Inn and tickets to The Fortune Teller's Ball. Celebrate downstairs, then head up to your cozy room when the night is done!

✨ From Christmas Eve traditions to a magical New Year's Eve, there's no better place to spend the holidays than Chatham, Cape Cod.

🎁 Book your holiday stay and explore our Activities & Events Calendar for all the festive details at bit.ly/4euDHPL or tap the website link in our bio.

10/28/2026

Your quintessential New England autumn escape awaits at the historic Wayside Inn in Chatham. Experience the tranquility and timeless beauty of Cape Cod. Book your fall getaway and create lasting memories.

10/25/2026

Celebrate Thanksgiving on Cape Cod with our annual Thanksgiving Dinner Buffet at Wild Goose Tavern!

Running from 11 AM to 4 PM for $155 per person (including w**e and ch*****ne), guests can gather around the table to enjoy traditional carving, pasta, and waffle stations alongside fresh shrimp and oysters right in the heart of downtown Chatham.

Visit https://bit.ly/48b6PY1 or tap the link in bio to see menu.

10/23/2026

Embrace cozy nights and the charming ambiance of Chatham this late October. Sip warm drinks by the fireplace, explore unique local shops, and savor delicious culinary finds.

Wayside Inn is your perfect home away from home.

10/18/2026

🎃🍷 Eat, drink & stay spooky in Chatham this Halloween!

Make a weekend of it at Chatham Wayside Inn and celebrate Halloween on Cape Cod with a night of delicious food, live music, and spooky fun right downstairs at Wild Goose Tavern!

👻 Saturday, October 31 | 8 PM–Close

Kick off the evening with our special Spanish Tapas Halloween Dinner, featuring shareable bites perfect for your favorite ghouls. Then stick around for the Monster Mash, live music, and a costume contest with prizes announced at 10:30 PM! 🎸🏆

The best part? After a night of Halloween revelry, your cozy room is just steps away. No broomstick required! 🧹

🍽️ Explore the event: bit.ly/3P0qovR
🛏️ Book your Halloween getaway: bit.ly/4euDHPL

10/16/2026

Join us for a nice getaway this week. You can make us your home away from home. Look at everything going on this weekend.

🍂 YOUR CAPE COD WEEKEND GUIDE! 🦪🍁

Looking for something fun to do on Cape Cod this weekend? There’s no shortage of fall festivities, delicious local food, live music, and community events!

🎶 FRIDAY, OCTOBER 16
Kick off the weekend with a walk through Kate Gould Park for Pumpkin people in the park, have a nice dinner in one of Chatham's many restaurants and listen to some live music at the local bars. All these activities are within walking distance of the Inn.

🍻 SATURDAY, OCTOBER 17
🍁 Chatham Oktoberfest | 11 AM–5 PM
🍺Wild Goose Tavern Biergarten
🦪 Wellfleet OysterFest | Celebrate Cape Cod’s famous oysters, local vendors, food, and entertainment!

🚲 SUNDAY, OCTOBER 18
🎉 Hyannis Open Streets | 12–4 PM
🦪 One last chance to enjoy Wellfleet OysterFest before the weekend wraps up!

Whether you're looking for family fun, great food, local shopping, or live entertainment, Chatham Wayside Inn is an amazing home away from home for you!📍512 Main St Chatham, MA 02633.

10/16/2026

Experience the breathtaking blend of fall foliage and coastal charm in Chatham this October! Take scenic strolls, breathe in the crisp ocean air, and soak up vibrant autumn hues. Wayside Inn is your perfect home base for all your leaf-peeping adventures.

10/09/2026

🍺🥨 Chatham is going Bavarian! Join us Saturday, October 17 for one of the Lower Cape’s favorite fall traditions—Chatham Oktoberfest!

Celebrate in downtown Chatham with the community festivities at Kate Gould Park & the Town Hall Parking Lot, then keep the Oktoberfest fun going at Wild Goose Tavern. We’re transforming our Main Street Lounge into a Bavarian-style Biergarten with:

🍻 Authentic German b**r & cuisine
🎶 Live music from The Mad Bavarians
🥨 Souvenir steins & two-person Das Boots
💪 Stein Hold competitions for men, women & kids
🏆 Prizes for the best Bavarian attire

Grab the lederhosen, dust off the dirndl, and get ready to prost! your way through a perfect fall Saturday in Chatham. 🍂🍺

📅 Saturday, October 17
📍 Wild Goose Tavern | 512 Main Street, Chatham

10/09/2026

Come Join us tonight and tomorrow for a quick retreat into a beautiful fall weekend. We have so much to do on the Cape that is sure to be a fun time. We would love to be your home away from home for the weekend.

Friday:
🎃First Congregational Church Pumpkin Patch Chatham, MA🎃
🍎Apple picking and Corn Maze at Crow Farms Sandwich, MA🍎
🌽Bartletts Farm Stand West Barnstable, MA🌽
📽Chatham Orpheum theatre Chatham, MA📽

Saturday:
🎶Outermost Roots & Blues Festival Orleans, MA Oct 10th🎶
🍎Apple picking and Corn maze at Crow Farms Sandwich, MA🍎
🎃First congregational Church Chatham Pumpkin Patch Chatham, MA🎃
🐂Taylor Bray Farms Fall Festival Yarmouth Port🐏
🍒Annies Crannies Cranberry harvest tour Dennis, MA🍒
🎭Cape Rep Theatre "Fall of the house of Usher" Brewster, MA🎭
🎨Paint and Learn at Monomoy National Wildlife Refuge Chatham, MA🎨

10/07/2026

🎃🍂 Coming soon to Chatham: the Pumpkin People are taking over the park!

Starting October 14 through October 31, the beloved Pumpkin People in the Park returns to Kate Gould Park with creative, quirky, and photo-worthy displays made by local businesses and organizations.

Staying at Chatham Wayside Inn? You’ll be right in the heart of the fun! Wander over to see the Pumpkin People, explore Main Street surrounded by fall color, then head back to Wild Goose Tavern for lunch, dinner, or a seasonal drink. 🍁

Planning an October getaway to Cape Cod? Come see Chatham get into the Halloween spirit! 🎃

Address

512 Main Street
Chatham, MA
02633

Telephone

+15089455550

Website

http://www.waysideinn.com/

Alerts

Be the first to know and let us send you an email when Chatham Wayside Inn posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.