Local Dining and Entertainment
Christmas by the Sea
NOTE THIS IS FOR FRIDAY, 12/11, ONLY! If you're looking to get festive, head over to Main Street for the Holiday Christmas Stroll! See all the shops in their holiday best. Head over to the Chatham Community Center (702 Main Street) at 5:30pm to see a light parade with Santa, followed by the tree lighting at Sears Park (intersection of Main Street and Seaview Street) at 5:45pm! Horse and carriage rides will also be available starting at 6pm at the Town Hall Entrance (549 Main Street).
Chatham Bars Inn
If you're looking for your upscale Cape moment, this is it. You can still enjoy the stunning decor and sip on delicious cocktails without breaking the bank!
Chatham Squire
Paxton's favorite place to be - a quintessential dive bar and local favorite. If you're looking for a drink and solid vibes you gotta make your way over. He recommends the Costello's 50/50 if you do!
Impudent Oyster
Paxton's favorite meal in Chatham! Classic Cape Cod lunch and dinner spot housed in a renovated church. If you're hungry, stop on in, you won't be disappointed! Note that you should look to make a reservation ahead of time to ensure you can be seated.
Chatham Pier Fish Market
Where Jenna goes to spot seals! Also happens to be home to the best clam chowder and lobster rolls on Cape Cod.
Wild Goose Tavern
Located in the Chatham Wayside Inn, Wild Goose is classic Cape Cod upscale casual. The menu ranges from light bites to pub-style favorites, and the renovated bar is a great place to post up!
Mom & Pops Burgers
Mom & Pops is a must-try if you're on the hunt for a good burger. However, Paxton's mom has some advice to share, "don’t overlook their chicken tenders—they're just as popular and definitely worth ordering!"
Red Nun Bar & Grill
Classic pub fare if you're feeling all fished out!
Carmine's Pizza
A small pizza joint known for excellent pizza—definitely one of the best in town. This place is all about takeout, making it the perfect stop for a quick and tasty meal to enjoy at home or on the go.
Del Mar Bar & Bistro
Del Mar is where upscale meets lively. A favorite for locals and visitors alike, the menu features fresh seafood, bistro favorites, and thin-crust wood-fired pizza. If you stop in make sure you check out their standout cocktails and wine list!
Bluefins Sushi & Sake Bar
Yes, the sushi is excellent—but the surprises are in the rest of the menu. The Pad Thai is crave-worthy, and the Hoisin-Glazed Baby Back Ribs are unforgettable. Great for sharing plates and date nights in downtown Chatham.
Chatham Filling Station
Retro diner vibes + amazing food = Jenna and Paxton's ideal place
Brax Landing Restaurant
Old school restaurant with a gorg view of the water!
Larry's PX
Looking for a breakfast spot on Sunday morning? We got you covered! Rumor has it this place serves up the best omelette on Cape Cod. Worth a visit, in Jenna's opinion!
Hangar B Eatery
This gem is located right at the airfield and has a reputation for using top-tier ingredients. The best part, you get breakfast AND a show. Watch small planes take off and land as you sip your coffee.
Cape Cod Coffee @ Chatham Perk
Start the party weekend off right with great coffee, a light bite or two and a relaxed coastal vibe!
Snowy Owl Coffee Espresso Bar
"Congratulations! You did it! The world's best cup of coffee!" - Buddy the Elf or Paxton about this place
Hey Joe and Jam
Guaranteed good vibes (and better coffee)!
Three Fins Coffee & Cacao Factory
If sipping your coffee in a renovated swimming pool is your vibe!
Chatham Candy Manor
If you've got a sweet tooth like Jenna, this is the place to be! Stop in to grab some delicious homemade fudge, chocolates, gummies and more. And don't leave without a cup of hot cocoa!