Chatham Vacation Planner

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 ~

Le Petite Day Spa

It's time for just you... Le Petite offers a variety of massage and skin treatments. Experience the latest innovations in massage therapy, hot stone massage, parafin foot wraps and facials. Rejuvenate in elegant surroundings and a relaxing atmosphere.

Categories: Day Spas

35 Cross Street, Chatham ~ (508) 945-9909 ~

Chatham’s family restaurant with a multi-cultural menu and entertaining cast including both crew and customers, the Squire is the place everyone looks for when they visit Chatham.

Categories: Casual Dining

487 Main Street, Chatham ~ (508) 945-0945 ~

Monomoy Island Ferries

Join Captain Keith Lincoln aboard the Rip Ryder for some of the best ocean fun and adventure available on Cape Cod. We invite you to come along for a day of exploration off the coast of Chatham, Cape Cod. Take one of our 90 min. Seal Cruises to see Chatham’s best known residents, the Grey Seals. Hiking, fishing, exploring or just relaxing seem... show more Join Captain Keith Lincoln aboard the Rip Ryder for some of the best ocean fun and adventure available on Cape Cod. We invite you to come along for a day of exploration off the coast of Chatham, Cape Cod. Take one of our 90 min. Seal Cruises to see Chatham’s best known residents, the Grey Seals. Hiking, fishing, exploring or just relaxing seem more your idea of a great day? Take our water taxi to either Monomoy Island or South Beach leaving from the Monomoy National Wildlife Refuge. For information and reservations ~ 508-237-0420. hide

Categories: Sightseeing & Tours

30 Wikis Way, Chatham ~ (508) 237-0420 ~

Where The Sidewalk Ends

Where the Sidewalk Ends Bookstore, is a mother-daughter bookstore in a welcoming, two-story "antique" barn. Comfortable fireside and outdoor seating provide relaxing places for browsing, sipping coffee, and using free Wi-Fi.

Categories: Bookstores

432 Main Street, Chatham ~ (508) 945-0499 ~

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 ~

What's For Dinner?

WHY COOK ON VACATION? Personal chef Bob Hessler has been preparing gourmet meals for Chatham renters and year-round residents since 2006. Rather than waste your vacation in the kitchen, allow Bob to prepare your meals for you. Planning a special event or celebration? He will do that too! A personal chef costs less than many take-out meals or going... show more WHY COOK ON VACATION? Personal chef Bob Hessler has been preparing gourmet meals for Chatham renters and year-round residents since 2006. Rather than waste your vacation in the kitchen, allow Bob to prepare your meals for you. Planning a special event or celebration? He will do that too! A personal chef costs less than many take-out meals or going to a restaurant. The menu is tailored to your tastes, needs, and diet. The fee is $75.00 per hour, which includes shopping, preparation, and clean-up but does not include the cost of the food. hide

Categories: Catering

PO Box 567, N. Chatham ~ (508) 945-0632 ~

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 ~

Now in our 11th year, Chatham Coffee Company has become the lower Cape's number one source for locally roasted coffees from around the world. We have consistently been voted best coffee shop and deli in Chatham during that time.

We are open year round. WiFi available.

Categories: Bakeries/Coffee Shops

307 Orleans Road, North Chatham ~

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 ~