RestaurantsPortland

Leeward

Leeward: Restaurant in Portland

(377)
Restaurant$$$
Leeward
Leeward

Why Eat

Why Leeward

Leeward is an informal Italian spot in Portland where the kitchen turns out house-made pasta and thoughtful seasonal dishes. The crowd skews serious about food but the vibe stays relaxed. Prices run upwards of $100 per person with drinks and dessert, and it's worth the spend.

  • House-made pasta is the real deal, especially the gnocchi.
  • Seasonal menu means different reasons to return throughout the year.
  • You can watch the kitchen work from the chef's counter.
  • Staff knows the menu and makes solid recommendations.

Menu

What to order

Start with gnocco fritto if it's available. The agnolotti (stuffed pasta) and rigatoni with ragù are pasta foundations done right. Try whatever seasonal pasta special is running that night. The savoy cabbage salad with anchovy-horseradish vinaigrette is a surprise hitter. For dessert, the carrot cake and panna cotta both reward careful attention.

At a Glance

At a glance

Best for

Date night, special occasions, pasta lovers.

Price range

$$

Details

85 Free St, Portland, ME 04101
(207) 808-8623
leewardmaine.com

Opening Times

MonClosed
Tue5:00 – 9:00 PM
Wed5:00 – 9:00 PM
Thu5:00 – 9:00 PM
Fri5:00 – 9:00 PM
Sat5:00 – 9:00 PM
SunClosed

Atmosphere

The room

Tight room, warm lighting, the kind of place that hums but doesn't shout. You're close to other tables and close to the kitchen, which is half the point.

Reviews

What guests say

Guests come back repeatedly and bring it up for special occasions. One recent visitor called the gnocchi the best they'd ever had. Regulars praise how well the kitchen handles gluten-free requests and how the menu captures the season. People notice the staff genuinely seems to enjoy the work.

Guides

Restaurants

Nearby restaurants

All Restaurants

Hotels

Nearby hotels

$$$

Hotel

Portland

Pearl of Portland

Beautifully renovated two-bedroom apartments in Portland's walkable East End. Full kitchens, laundry, parking. 9.7/10 from guests.

$$$

Hotel

Portland

Peaceful Oasis on Munjoy Hill

Spacious 3-bedroom apartment on Portland's East End. Free parking, full kitchen, steps from beaches and downtown. 9.7/10 from recent guests.

$$$

Hotel

Portland

The Cushman

Spacious 3-bedroom townhome in Portland's West End. Full kitchen, private entrance, steps from Victoria Mansion and downtown. Ideal for families and groups.

$$$

Hotel

Portland

Knock on Wood

Spacious two-bedroom apartment in downtown Portland with full kitchen, fireplace, and pet-friendly policy. Walking distance to restaurants and attractions.

$$$

Hotel

Portland

The Brew House

Spacious one-bedroom apartment above a craft brewery in Portland's East End. Walking distance to restaurants, shops, and waterfront. 9.5/10 from 65 guests.

$$$

Hotel

Portland

State of Charm

Two-bedroom apartment in Portland's West End, steps from downtown shops and restaurants. Full kitchen, walkable neighborhood.

$$$

Hotel

Portland

West End Inn

Historic boutique inn in Portland's West End. Acclaimed breakfast, walkable neighborhood, attentive hosts. Perfect for couples exploring Maine's coast.

$$$

Hotel

Portland

Heart of the West End #3

Spacious two-bedroom apartment in Portland's West End. Walk to Congress Street restaurants, museums, and downtown. Pet-friendly with parking.

$$$

Hotel

Portland

Best Bower

A beautifully designed boutique inn on Congress Street with spacious rooms, private courtyard, and walking distance to Portland's Old Port, restaurants, and waterfront.

$$$

Hotel

Portland

The Highland House

Spacious 3-bedroom house in quiet Portland neighborhood. Full kitchen, free parking, pet-friendly. Walk to downtown and arts district.

$$$

Hotel

Portland

Longfellow Hotel

Elegant 5-star boutique hotel on Congress Street. Spa, on-site dining, complimentary town car, and walkable to Portland's best restaurants and shops.

$$$

Hotel

Portland

The Docent's Collection

Spacious, design-forward lofts in downtown Portland's Old Port. Full kitchens, soundproof rooms, and walkable access to restaurants and waterfront attractions.

All Hotels