Orleans Vacation Planner

Old Jailhouse Tavern

At the historic Old Jailhouse Tavern in Orleans, once used as the town lockup, we offer creative menu selections for lunch, dinner, late night fare and Sunday Brunch — all in a casual, comfortable atmosphere, beautifully landscaped and designed by an award-winning architect. Hosting a special function? Our Courthouse facility can accommodate 30... show more At the historic Old Jailhouse Tavern in Orleans, once used as the town lockup, we offer creative menu selections for lunch, dinner, late night fare and Sunday Brunch — all in a casual, comfortable atmosphere, beautifully landscaped and designed by an award-winning architect. Hosting a special function? Our Courthouse facility can accommodate 30 to 150 guests. hide

Categories: Casual Dining

28 West Road, Orleans ~ (508) 255-5245 ~

Rockin Robin Charters

Leaving from Rock Harbor, the Rockin' Robin, a 30' Boston Whaler, will take you fishing across Billingsgate Shoal, one of the most productive striped bass fishing spots on Cape Cod Bay. Please join us while you're staying on the Cape and enjoy the sun, fun, and the excitement that catching striper can only provide. Whether or not you're a seasoned... show more Leaving from Rock Harbor, the Rockin' Robin, a 30' Boston Whaler, will take you fishing across Billingsgate Shoal, one of the most productive striped bass fishing spots on Cape Cod Bay. Please join us while you're staying on the Cape and enjoy the sun, fun, and the excitement that catching striper can only provide. Whether or not you're a seasoned pro or have never fished before, you won't want to miss this! hide

Categories: Fishing Charters

Rock Harbor, Orleans ~ (774) 722-0974 ~

Blue Claw Boat Tours

Our 1-1/2 hr guided tour from Orleans, travels to Chatham and back along the historic waterway of Pleasant Bay once used by early pilgrims, pirates and Indians. Capt Rob will regale you with tales of the rich history and natural bounty of this pristine ecosystem. A lighthouse, seals, rustic beach camps, seaside mansions, deserted islands, and... show more Our 1-1/2 hr guided tour from Orleans, travels to Chatham and back along the historic waterway of Pleasant Bay once used by early pilgrims, pirates and Indians. Capt Rob will regale you with tales of the rich history and natural bounty of this pristine ecosystem. A lighthouse, seals, rustic beach camps, seaside mansions, deserted islands, and maybe a Great White shark are viewed along the way. Capt Rob (USCG licensed master of 30 years) and our vessel is USCG inspected. See why we are the fastest growing tour on Cape. Private custom cruises a specialty. hide

Categories: Sightseeing & Tours, Boat Cruises

235 Main Street, Orleans ~ (508) 240-5783 ~

Sea Howl Bookshop

Real live books sold here. We carry a thoughtfully curated selection of new & used books, along with greeting cards, notebooks, stickers, art prints, puzzles, and more unique, bookish finds.

Categories: Bookstores

46 Main St, Orleans ~ 508-255-3343 ~

Come in for excellent pizza, salads, subs & more!

Categories: Pizza

180 Rt 6A, Orleans, MA, Orleans ~ (508) 255-7160 ~

Balanced 4 Fitness

"Your Complete Vacation Fitness Fix" East Orleans Studio offering Private Reformer & Small Group Training (3-9) in Pilates "Classical Method" Tower Springs, Chair, Pilates Mat, SPINNING, Bosu and More. By Appointment 509-240-2739

Categories: Other Fitness/Wellness

15 Pineneedle Way, Orleans ~ (508) 240-2739 ~

Focalpoint Studio

Cape Cod Photographer Bob Tucker has been specializing in Family Portraits at the Beach since 1973. Now's the time to book your family's portrait. Whether you choose the Atlantic surf, one of the Cape Cod Bay beaches or a serene natural setting as your backdrop, your family's photograph will be a cherished momento. Or, use it on your Christmas... show more Cape Cod Photographer Bob Tucker has been specializing in Family Portraits at the Beach since 1973. Now's the time to book your family's portrait. Whether you choose the Atlantic surf, one of the Cape Cod Bay beaches or a serene natural setting as your backdrop, your family's photograph will be a cherished momento. Or, use it on your Christmas card this year ~ always appreciated especially by long distance family and friends. You may also want to celebrate a special occasion, such as a milestone anniversary or family reunion, by capturing it in a professionally shot photograph. Focalpoint Studio also specializes in photo restoration and theatrical photography. hide

Categories: Photography & Video

56 Main Street, Orleans ~ (508) 255-6617 ~

Award winning dining overlooking Town Cove - enjoy a lobster salad sandwich in the elegant O’Hagan’s Irish Pub or cocktails on the outdoor decks overlooking the Cove.

Categories: Waterfront Dining

3 Old County Road, Orleans ~ (800) 863-3039 ~

Nauset Surf Shop

Nauset Surf Shop is the oldest running surf shop on Cape Cod! Founded in 1965, the history of surfing for this shop began with wax, tees, bikinis and boards. Phil Clark, current owner, acquired Nauset Surf in 1970, straight out of college, and opened his first shop. Over the past 49 years Phil has grown the business.We thank this wonderful... show more Nauset Surf Shop is the oldest running surf shop on Cape Cod! Founded in 1965, the history of surfing for this shop began with wax, tees, bikinis and boards. Phil Clark, current owner, acquired Nauset Surf in 1970, straight out of college, and opened his first shop. Over the past 49 years Phil has grown the business.We thank this wonderful community and our awesome customers and employees for all the love, support and hard work! We look forward to supplying you with everything you need for a great day on the beach! hide

Categories: Other Shopping

2 Rt 6A Jeremiah Sq., Orleans ~ 508-255-4742 ~

The Rail

Grand opening in April 2021. Stop in for breakfast or lunch, sit out on the patio overlooking Main St., or grab n' go on your way to Nauset Beach. Open 7 days a week, 5am - 3pm.

Categories: Casual Dining

222 Main Street, Orleans ~ (774) 561-2161 ~