Chatham Vacation Planner

Skydive Chatham

Experience the thrill of a lifetime with a skydive over beautiful Cape Cod and its glorious beaches. Never skydived before? After tandem jump training, you will fly to 10,000 feet. Harnessed to your tandem instructor, you will freefall for about 45 seconds at over 120 MPH! Once your parachute is open, you will steer your parachute to a soft... show more Experience the thrill of a lifetime with a skydive over beautiful Cape Cod and its glorious beaches. Never skydived before? After tandem jump training, you will fly to 10,000 feet. Harnessed to your tandem instructor, you will freefall for about 45 seconds at over 120 MPH! Once your parachute is open, you will steer your parachute to a soft landing. Ask about our weekday specials. hide

Categories: Extreme Sports

240 George Ryder Road, Chatham ~ (508) 348-1422 ~

Millie's of Chatham

Shop all of New England beneath one roof! At Millie's of Chatham General Store, we offer unique and specialty items that are New England made products and that you can’t find just anywhere such as salsas, hot sauces, maple syrup, Cape Cod honey, pasta, Nantucket Baskets, note cards, jewelry, toys, penny candy, prints, candles, apothecary items,... show more Shop all of New England beneath one roof! At Millie's of Chatham General Store, we offer unique and specialty items that are New England made products and that you can’t find just anywhere such as salsas, hot sauces, maple syrup, Cape Cod honey, pasta, Nantucket Baskets, note cards, jewelry, toys, penny candy, prints, candles, apothecary items, wallets, kitchenware, and much more. hide

Categories: Gift Shops

1291 Main Street "The Cornfield", Chatham ~ (508) 945-2900 ~

For pizza, subs, calzones, and more, walk in or call ahead and your order will be waiting for you! Serving Beer and Wine too.

Categories: Pizza

1200 Main Street, Chatham ~ (508) 945-9070 ~

Tanika's

Categories: Gift Shops

636 Main St, Chatham ~ (508) 945-1986 ~

Chatham Orpheum Theater

The original Orpheum Theater opened in 1916 as Chatham's first and only movie house. From the early days of silent films through the blockbuster era of JAWS, our Main Street movie theater was a magical place for 72 years — a year-round destination where generations of Cape Cod families and summer visitors could enjoy gripping dramas, slapstick... show more The original Orpheum Theater opened in 1916 as Chatham's first and only movie house. From the early days of silent films through the blockbuster era of JAWS, our Main Street movie theater was a magical place for 72 years — a year-round destination where generations of Cape Cod families and summer visitors could enjoy gripping dramas, slapstick comedies, joyous musicals or swashbuckling adventure films week after week. The Chatham Orpheum Theater holds a special place in the community and we are so very grateful for the support of those who believe in the importance of culture and the local programming we have all come to enjoy and incorporate into our lives hide

Categories: Movies

637 Main St, Chatham ~ (508) 945-0874 ~

Corner Store

The Corner Store is all about Fresh. Fast. Fun.

Makers of some of the best burritos, paninis and sandwiches on the Cape to eat-in or take-out on the go to the beach. Plus, check out their famous whoopie pies!

Categories: Casual Dining

1403 Old Queen Anne Road, Chatham ~ (508) 432-1077 ~

Chatham Bars Inn

Chatham Bars Inn has a variety of distinctive settings to accommodate wedding groups. All our ceremony and reception sites offer stunning views of the Atlantic Ocean.

Categories: Receptions

297 Shore Road, Chatham ~ (800) 527-4884 ~

hangar B eatery

Hangar B eatery is located at the Chatham Municipal Airport providing for a unique spot for breakfast and lunch. This spot is a hidden gem allowing views of small planes during take-off and landing while enjoying your meal. Brunch enthusiasts often come for our red flannel hash, lemon ricotta pancakes, or huevos rancheros.

Categories: Casual Dining

240 George Ryder Rd, Chatham ~ (508) 593-3655 ~

Pisces Restaurant & Bar

Celebrating its 15th season, this charming and intimate restaurant features Coastal Cooking with flavors gathered from around the world. Everything at Pisces is made fresh and to order. Although the menu features mostly seafood, there is also an excellent selection of non-seafood items available, including steak, chicken and vegetarian fare as... show more Celebrating its 15th season, this charming and intimate restaurant features Coastal Cooking with flavors gathered from around the world. Everything at Pisces is made fresh and to order. Although the menu features mostly seafood, there is also an excellent selection of non-seafood items available, including steak, chicken and vegetarian fare as well. Our menu changes frequently to take advantage of the freshest local and seasonal ingredients. Dinner is served nightly beginning at 5 pm April through October. Reservations are highly recommended. hide

Categories: Fine Dining

2653 Main Street, Chatham ~ (508) 432-4600 ~

Island Pursuit

Casual luxury sportswear for women and men. All your favorite designers including Lily Pulitzer, LaCoste, Vineyard Vines, Tommy Bahama, Agave Denim and Bugatchi Uomo along with a wide array of accessories including shoes, hats, jewelry and sunglasses.

Categories: Clothing & Accessories

482 Main Street, Chatham ~ (508) 945-3525 ~