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 ~

Adorn Cape Cod

At Adorn, we curate a collection of items we adore, including local fine art—featuring painters based right here in Orleans—along with home decor, textiles, accessories, greeting cards, ceramics, gifts, house plants, handcrafted jewelry, and much more. We are proud to support independent artists, designers, and makers, many of whom are local to... show more At Adorn, we curate a collection of items we adore, including local fine art—featuring painters based right here in Orleans—along with home decor, textiles, accessories, greeting cards, ceramics, gifts, house plants, handcrafted jewelry, and much more. We are proud to support independent artists, designers, and makers, many of whom are local to Cape Cod. Additionally, we offer a selection of fair trade goods, including our customer-favorite block print textiles and woven baskets. hide

Categories: Gift Shops

211 Main St, Orleans ~ 774.316.4245 ~

Orleans Cycle

Offering bike rentals for hourly, daily or weekly rates, Orleans Cycle is located on the Cape Cod Rail Trail in the center of Orleans. We rent new, high quality, road bikes, comfort bikes, hybrids, kids bikes, trailers, and tag-a-longs. Orleans Cycle sells new Trek and Specialized bicycles. All rentals include helmets and a map of the bike trail.... show more Offering bike rentals for hourly, daily or weekly rates, Orleans Cycle is located on the Cape Cod Rail Trail in the center of Orleans. We rent new, high quality, road bikes, comfort bikes, hybrids, kids bikes, trailers, and tag-a-longs. Orleans Cycle sells new Trek and Specialized bicycles. All rentals include helmets and a map of the bike trail. Cycling on Cape Cod is an excellent way to spend your vacation. You can bike to the freshwater ponds in Brewster to the south or to the National Seashore farther north. hide

Categories: Bike Rentals

26 Main Street, Orleans ~ (508) 255-9115 ~

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 ~

Goose Hummock Kayak Adventures

Operating for over 65 years, Goose Hummock Shop is Cape Cod's Largest Paddle Sports and Outdoors Super Store. Sales, Rentals and Instruction for Kayaks,Canoes and Stand Up Paddle Boarding. Our expert staff will take you on group marsh tours or give you private instruction to get you quickly and our rental fleet consists of over 125 brand name... show more Operating for over 65 years, Goose Hummock Shop is Cape Cod's Largest Paddle Sports and Outdoors Super Store. Sales, Rentals and Instruction for Kayaks,Canoes and Stand Up Paddle Boarding. Our expert staff will take you on group marsh tours or give you private instruction to get you quickly and our rental fleet consists of over 125 brand name kayaks, canoes and Stand Up paddle boards..always plenty to choose from! Our sales floor is stocked to the brim with the best brands Necky, Old Town,Bic, Ocean and more. Try before you buy- we are located right on beautiful Town Cove in Orleans
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Categories: Kayaking & Paddle Sports, Other Shopping

15 Rt 6A, Orleans ~ (508) 241-1137 ~

Orleans Bowling Center

Open Monday - Thursday 9 am to 9 pm, Friday 9 am to 10 pm, Saturday 9 am to 11 pm, Sunday 12 noon to 9 pm.

Categories: Amusements

191 Rt 6A, Orleans ~ (508) 255-0636 ~

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

Categories: Pizza

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

Hindsight Sportfishing

HINDSIGHT, is one of the largest and is the newest boat in our fleet. Full accommodations and very comfortable. Striped bass, bluefish and giant Bluefin tuna are our specialties. We also do whale watch trips as well as sight seeing tours of Cape Cod all the way to Provincetown. Sunset trips when available. We are located at Rock Harbor in Orleans.... show more HINDSIGHT, is one of the largest and is the newest boat in our fleet. Full accommodations and very comfortable. Striped bass, bluefish and giant Bluefin tuna are our specialties. We also do whale watch trips as well as sight seeing tours of Cape Cod all the way to Provincetown. Sunset trips when available. We are located at Rock Harbor in Orleans. Please visit our website at hindsightsportfishing.com. Or call us at 305.481.1291 hide

Categories: Fishing Charters

Rock Harbor, Orleans ~ (305) 481-1291 ~

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 ~

Academy of Performing Arts

Offering classes in dance, music, theatre, outreach residencies, workshops, assemblies, and main stage Playhouse & School productions. Kids can perform weekly in July and August.

Categories: Performing Arts

120 Main Street, Orleans ~ (508) 255-3075 ~