Nautical Mile

With top-notch restaurants, fresh seafood and charter boats leaving daily on fishing trips, The Nautical Mile in Freeport is one of the hottest destinations for food and summer fun on Long Island. Located on Woodcleft Avenue, which runs along the west side of Woodcleft Canal, the waterfront strip features dozens of restaurants, bars, shops and recreational hot spots, making it the perfect destination for families and party-goers alike. “Walk a nautical mile in Freeport town, and you’re sure to feel up instead of down,” as the Freeport Chamber of Commerce puts it. During the day, visitors to The Nautical Mile can find some of the best seafood on LI, check out the shops or simply enjoy the waterfront vistas. After the sun goes down, it transforms into a premiere party destination with a lively nightlife scene.

E.B. Elliot's thumbnail viewE.B. Elliot's $$-$$$ Waterside dining / Live music / Wi-Fi / Open year round

This top rated restaurant features two story dining, indoor bar, and large outdoor bar. The emphasis is seafood, but there’s something here for everyone, even the kids.

Blue 42 thumbnail viewBlue 42 $-$$ Outdoor Dining / Water views / Open year round

This Nautical Mile restaurant features one outdoor and two indoor dining areas. Menu offers pasta, poultry, seafood, steak & fowl.

Nautilus Cafe thumbnail viewNautilus Café $$$ Indoor dining only / Water views / Open year round

Spacious dining room with lots of windows and water views. Menu heavy on steaks and fish with some veal, poultry, and fowl for good measure. Extensive wine list. Famous for their homemade banana bread.

Landshark thumbnail viewLandShark $-$$ Waterside dining / Live music

This unique outdoor only raw bar / bar & grill is great for a beer and a bite right on the water. Excellent bar scene, but probably not the place for kids.

Crabshack thumbnail viewThe Crabshack $-$$ Open year round

A fixture on the Nautical Mile for 30 years, the Crabshack is all about fresh fish at reasonable prices. Menu offers classic baked, broiled, and fried fish, as well as a large selection of Italian style favorites. And yes, they serve crabs too.

Ralphs thumbnail viewRalph's Italian Ices

Speaks for itself...

Water Lilly's thumbnail viewWater Lilly's $-$$ Outdoor dining / Live music

One of my favorite Nautical Mile restaurants. Great for a beer, a burger, and a little live music. Home of Freeport's Famous Chili and the Special Burger, Water Lilly's serves up fresh fish, sandwiches, and low carb specials as well.

River House Grill thumbnail viewRiver House Grille $$-$$$ Street & waterside dining / Live music / Open year round

Menu offers contemporary, traditional, Cajun, and Thai style seafood alongside steaks and burgers. Indoor bar faces Woodcleft canal for some nice water views. Indoor dining room can be uncomfortably loud when band is playing.

JC Cove thumbnail viewJC Cove $-$$ Waterside dining / Live music / Open year round

I can't say much about this place. I've never eaten here and when I walked in to take pictures for this article I was treated with indifference by the manager. Looks like a nice place though.

Villa's Kitchen thumbnail viewVilla's Kitchen $ Outdoor dining

Italian pizzeria/restaurant serving pizza, burgers and chicken. An antidote, if you will, to the typical Nautical Mile menu.

Jeremy's Ale House thumbnail viewJeremy's Ale House $-$$ Waterside dining / Live music / Wi-Fi / Open year round

A pub in the true sense of the word. Don't wait to be seated, order your food at the bar. 16 brews on tap, bar menu with seafood classics. Donate you bra to the collection hanging from the ceiling and drink free beer all night.

Waterfront Tavern thumbnail viewHurricane Harry's $-$$ Waterside dining / Live music

Beautiful dining room and bar overlooking the canal. Spacious and clean waterside & street side dining.

Hershey's Ice Cream thumbnail viewHershey's Ice Cream

Need I say more?

Otto's Sea Grill thumbnail viewOtto's Sea Grill $$-$$$ Waterside Dining / Live music

Another one of my favorite Nautical Mile restaurants. Run by the same family now for nearly 80 years, Otto's is one of the hot spots. Good food, music, and spacious outdoor dining keep me coming back. And, this is where Rocky the Dancer hangs out.

Rachel's Waterside Grill thumbnail viewRachel's Waterside Grill $$-$$$ Waterside dining / Heated deck / Open year round

Excellent seafood, steaks, burgers and wraps keep people coming back to Rachel's. Try their Japanese Tuna "Nachos" made with rice paper, and order your fish prepared in any of 5 different styles. Spillover music from Otto's is at an enjoyable level.

Bonito Hibachi & Sushi Bar thumbnail viewBonito Hibachi & Sushi Bar $$-$$$ Waterside Dining

The only sushi restaurant on the Nautical Mile. Extensive sushi, sashimi and hibachi menu. Polite service from Japanese waitresses in traditional dress. Ask for a tatami room on the waterside wall for a beautiful dining experience.

Bracco's thumbnail viewBracco's Clam & Oyster Bar $-$$ Waterside dining / Live music / Open year round

An extension of Cap't Ben's Fish Dock Bracco's serves what the could be the freshest fish on the Nautical Mile. If you're a fan of Ipswich clams you'll find them here. Huge outdoor dining and bar area. Quick service from polite staff. Boisterous crowd.

Hudson & McCoy thumbnail viewHudson & McCoy Fish House & Bar $$$ Outdoor dining / Live music

This lively restaurant features fresh fish, great steaks, poultry, and pasta in a beautiful 1940's fish house setting. Raw bar offers a selection of regional oysters. Enjoy an oversize martini or fresh squeezed screwdriver while listening to live music Thursday through Sunday.

Margo & Frank's Mermaid thumbnail viewMargo & Frank's Mermaid $$ Waterside dining

CLOSED! This place was a throwback to the 70's that served fresh seafood broiled, fried and Italian styles. Kid's menu and a few token dishes for land lubbers. All deserts were made on premises. Large deck on the canal. Slips were available for those arriving by boat.

Schooner Restaurant thumbnail viewThe Schooner Lobster & Fish House $$-$$$ Waterside dining / Live music / Closed month of January

Seating for 350 makes this the largest of the Nautical Mile restaurants. Multiple dining rooms and decks, extensive up to date menu offers something for everyone and lobsters up to 4 pounds. Outdoor seating overlooks Middle Bay.