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Sydney & Jake

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Things To Do

Dowses Beach

Dowses Beach

348 East Bay Road, Osterville, MA 02655

Dowses beach is the public beach in town! It's beautiful and has a ton of parking.

Pickle Ball or Tennis at Barnstable Town Tennis Courts

Pickle Ball or Tennis at Barnstable Town Tennis Courts

760 Osterville West Barnstable Road, Barnstable, MA 02648

Head over to the public town courts for some pickle ball or tennis!

The Farmer's Market at Osterville Historical Society

The Farmer's Market at Osterville Historical Society

155 West Bay Road, Barnstable, MA 02655

There is a farmer's market at the Osterville Historical Society (also where our welcome party is!) every Friday from 9am-1pm. Stop by to check out the local goods!

Fancy's Market

Fancy's Market

699 Main Street, Barnstable, MA 02655

This is our favorite spot in town for a sandwich and some snacks!

Chart Room at Crosby's

Chart Room at Crosby's

330 West Bay Road, Barnstable, MA 02655

Grab a bite and a drink at the Chart Room and watch the boats pass by the marina. (Pro tip: try some local oysters (how Osterville got its name!) and a Painkiller)

Four Seas Ice Cream

360 South Main Street, Barnstable, MA 02632

The best ice cream in the world. Try the Mocha Chip!

CRISP

791 Main Street, Barnstable, MA 02655

Our favorite spot for pizza! Fan favorites are the Angry Beekeeper, the Farm Egg, and the Caliente! You can also order take out from Crisp Too! across the street.

The Fox Hole

753 Main Street, Barnstable, MA 02655

Our local dive bar (yes, it is underneath the veteran's center). Stop in for some refreshingly cheap drinks and a round of pool.

Wimpy's Seafood Cafe

752 Main Street, Barnstable, MA 02655

Treat yourself to a lobster roll at Wimpy's!

Hometown Juice & Co

3 Wianno Avenue, Barnstable, MA 02655

Fight your hangover with a freshly made juice or smoothie!

Kettle Ho Restaurant & Tavern

12 School Street, Barnstable, MA 02635

If you're up for a 15 minute drive, pop over to the Kettle Ho in Cotuit for a beer and try to spot your college flag on the walls!

Five Bays Bistro

825 Main Street, Barnstable, MA 02655

Try Five Bays Bistro if you are looking for an upscale sit down dinner.

AMIE Bakery

1254 Main Street, Barnstable, MA 02655

Our go-to spot for coffee and croissants!

Anejo Mexican Bistro

599 Main Street, Barnstable, MA 02601

A fun Mexican restaurant in downtown Hyannis with great margaritas and a fun atmosphere!

For all the days along the way
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