A Foodie Weekend in Portland

Portland punches way above its weight class when it comes to food. This small coastal city has more James Beard award winners per capita than almost anywhere in America. The proximity to ocean, farms, and passionate chefs creates a dining scene that rivals cities ten times its size.

Day 1: Donuts to Oysters

Morning: Sweet Beginnings

• The Holy Donut (8am) - Maine potato donuts, multiple locations
  • Must-try: Dark Chocolate Sea Salt, Fresh Blueberry
  • Tip: Weekdays less crowded than weekends
  • Price: $2-3 per donut
• Walk the Old Port (9am) - Work off those donuts, cobblestone streets
• Coffee at Speckled Ax (10am) - Roasted in-house, excellent pour-overs

Late Morning: Portland Head Light

• Drive to Fort Williams Park (20 min)
• Portland Head Light (11am) - Maine’s most photographed lighthouse
• Beach walk - Rocky shores, tide pools
• Light lunch at Bite Into Maine (Cape Elizabeth) - Lobster roll food truck

Afternoon: Beer & Cheese

• Return to Portland (1pm)
• Check into hotel - Unload bags, freshen up
• Bard Coffee (2pm) - Third-wave coffee roasting
• Cheese shop hop (3pm):
  • Browne Trading Market - Caviar, smoked fish, cheese
  • Micucci’s Grocery - Italian market, fresh pasta
  • Or: Rosemont Market - Gourmet provisions

Late Afternoon: Brewery Tour

• Allagash Brewing Company (4pm tour, free, reserve ahead)
  • Tasting room
  • Learn about Belgian-style brewing
  • Must-try: Allagash White
• Or: Bissell Brothers - Hazy IPAs, food trucks outside

Evening: Oyster Heaven

• Eventide Oyster Co. (5:30pm, arrive early or reserve if possible)
  • Brown butter lobster roll - The one that changed lobster rolls
  • Oysters - Rotating selection from Maine waters
  • Uni shooters - If you’re adventurous
  • Budget: $60-80/person
• Or: Fore Street (If you got reservation weeks ago)
  • Wood-fired everything, legendary
  • James Beard winner
• After-dinner walk - Old Port is beautiful at night
• Nightcap at Novare Res - Belgian beer bar, 500+ selections

Lodging: Press Hotel, Portland Harbor Hotel, or Westin Harborview

Day 2: Brunch to Small Plates

Morning: Harbor Breakfast

• Standard Baking Co. (7:30am) - Get there when doors open
  • Morning buns - Cinnamon-sugar perfection
  • Almond croissants - Legendary
  • Coffee - Barista Coffee (they roast for many top restaurants)
  • Sit by windows - Watch Commercial Street wake up
• Working waterfront walk (8:30am) - Fishing boats, lobster co-ops
• Portland Fish Pier - See the catch coming in

Late Morning: Markets & Food Shops

• Portland Farmers Market (Saturday 9am-1pm, Deering Oaks)
  • Local produce, cheese, bread
  • Meet the farmers
  • Samples everywhere
• Or: Food tour of Congress Street (weekdays)
  • Rosemont Market - Prepared foods, provisions
  • Aurora Provisions - Sandwiches, salads, sweets
  • Tandem Coffee - Best coffee in Portland (many say)

Afternoon: Lunch & Peninsula Exploration

• Lunch options (12:30pm):
  • Duckfat - Belgian fries in duck fat, paninis
  • Atsuko - Japanese small plates
  • Pai Men Miyake - Ramen, noodles
• Eastern Promenade walk (2pm) - Bay views, 2-mile trail
• Leisure time (3pm):
  • Nap at hotel
  • Shop Exchange Street
  • Visit Portland Museum of Art

Early Evening: Cocktails & Snacks

• Cocktail hour (5pm):
  • The Honey Paw - Asian-inspired, inventive drinks
  • Hunt + Alpine Club - Craft cocktails, snacks
  • Vena’s Fizz House - Creative cocktails, bottle shop
• Or: Wine at High Roller Lobster Co. - Champagne and lobster

Dinner: Small Plates

• Central Provisions (7pm reservation, book weeks ahead)
  • Seasonal small plates
  • Share everything
  • Chef’s counter seats (walk-in only, arrive at 5pm)
  • Budget: $70-100/person
• Backup options (if no Central Provisions reservation):
  • Emilitsa - Greek small plates
  • Tipo - Italian pasta and wood-fired
  • The Grill Room - Farm-to-table elegance

Late Night

• Gelato at Gorgeous Gelato - Multiple flavors, by the Old Port
• Or: Ice cream at Mount Desert Island Ice Cream - Creative flavors
• Bar hop Exchange Street - Several cocktail bars

Lodging: Same as Day 1

Day 3: Markets to Departure

Morning: Final Bites

• Brunch options (9am):
  • Becky’s Diner - Classic waterfront diner since 1991
  • Blue Spoon - Upscale brunch, reservations recommended
  • Dutch’s - Breakfast sandwiches, creative morning fare
  • Hot Suppa - Southern-style brunch
• Post-brunch walk (11am) - Munjoy Hill neighborhood

Late Morning: Last Tastes

• Public Market House (11:30am) - Indoor food hall
  • Curated cheese and provisions
  • Sample local products
  • Pick up gifts to take home
• Or: Visit specialty shops:
  • Angela Adams - Maine designer home goods
  • Ferdinand - Homewares and gifts
  • Renys - Maine discount department store (Portland location)

Afternoon: Departure Prep

• Lunch to go (12:30pm):
  • Susan’s Fish-N-Chips - Classic fried seafood
  • Otto Pizza - Inventive slices
  • Scratch Baking - Sandwiches, sweets
• Depart Portland or extend (see below)

Essential Information

Best Time to Visit

Summer (June-August): Warmest weather, outdoor dining, all restaurants open Fall (September-October): Cooler, fewer tourists, harvest season menus Winter (November-March): Cozy dining, some restaurants closed Mondays Spring (April-May): Mud season, but restaurant deals, fewer crowds

Restaurant Reservations

Book Weeks Ahead:

• Fore Street
• Central Provisions
• Eventide (accepts some reservations now)
• Hugo’s

Book Days Ahead:

• The Grill Room
• Tipo
• Emilitsa

Walk-In Friendly:

• Duckfat (expect waits)
• Atsuko
• The Holy Donut
• Most breakfast spots

Getting Around

Parking: Use garage ($20-30/day) and walk everywhere Uber/Lyft: Available but not always quick Walkability: Old Port/downtown extremely walkable Brewery visits: May need car/Uber (industrial areas)

What Makes Portland Special

• James Beard winners: Fore Street, Hugo’s, Eventide
• Farm-to-table: Most menus change seasonally
• Seafood: From the docks to your plate same day
• Immigrant cuisines: Vietnamese, Somali, Italian communities
• Craft beer: 20+ breweries in metro area
• Coffee culture: Roasters everywhere

Dietary Accommodations

Vegetarian/Vegan: Excellent options at most restaurants

• Green Elephant (all vegetarian)
• Handmade vegetarian/vegan pasta at Tipo
• Most restaurants mark V/VG options

Gluten-Free: Many restaurants accommodate

• Ask servers, most kitchens adapt
• Scratch Baking has GF options

Allergies: Portland chefs take allergies seriously, communicate clearly

Budget Estimate (per person, 2 sharing)

Lodging: $300-500 (2-3 nights) Meals: $250-400 (mix of casual and upscale) Drinks: $80-150 (cocktails, beer, wine) Activities: $50-100 (brewery tours, markets) Parking: $40-60 Total: $720-1,210 per person

Budget Tips

• Lunch is cheaper: Same restaurants, lower prices
• Happy hours: Many bars have 4-6pm specials
• Counter seats: Central Provisions walk-in counter
• Food trucks: Bite Into Maine, Gorgeous Gelato
• BYOB: Some restaurants allow (call ahead)
• Weekday deals: Tuesday-Thursday often has specials

Beyond Lobster Rolls

Yes, get a lobster roll (Eventide’s brown butter version is transcendent), but don’t miss:

Vietnamese: East Ender - Pho and banh mi Ramen: Pai Men Miyake - Multiple locations Italian: Tipo, Emilitsa (Greek-influenced) Pizza: Otto, Slab Southern: Hot Suppa Asian Fusion: The Honey Paw Bakeries: Standard Baking, Scratch Baking, Two Fat Cats

Extend Your Trip

Add a Day For:

• Freeport - L.L.Bean, outlet shopping, breweries
• Cape Elizabeth - More lighthouses, ocean views
• Casco Bay Islands - Ferry to Peaks Island or Great Diamond
• Coastal Maine Botanical Gardens - 1 hour north in Boothbay

Combine With:

• Midcoast itinerary - Continue north to Camden/Rockland
• Southern beaches - Head south to Ogunquit/Kennebunkport
• Western mountains - 90 minutes to Sebago Lake/Bethel

Pro Tips

1. Arrive hungry - Portions generous, share plates
2. Reservations: Book fine dining weeks ahead
3. Breakfast: Start early, bakeries sell out
4. Walk it off: Portland is compact and walkable
5. Brewery tours: Reserve online (free but limited)
6. Eventide: Arrive at 4:45pm for walk-in bar seats
7. Central Provisions: Try for chef’s counter walk-ins at 5pm
8. Sunday/Monday: Some restaurants closed, check first
9. Samples: Cheese shops, markets all offer tastes
10. Takeout: Many spots great for picnic provisions

Sample Meal Budget

Budget Day ($50-70):

• Breakfast: Holy Donut + coffee ($8)
• Lunch: Duckfat ($18)
• Dinner: Atsuko ($30)
• Drinks: Happy hour ($15)

Mid-Range Day ($100-130):

• Breakfast: Standard Baking ($12)
• Lunch: Bite Into Maine ($25)
• Dinner: Emilitsa ($60)
• Drinks: Cocktail bar ($25)

Splurge Day ($150-200):

• Breakfast: Blue Spoon brunch ($30)
• Lunch: Central Provisions lunch ($40)
• Dinner: Fore Street ($80)
• Drinks: Wine pairing ($50)

Why Visit Portland?

Portland has cracked the code: Take the freshest ingredients from ocean and farm, add passionate chefs who care about sourcing, stir in a community that supports independent restaurants, and you get something special.

This isn’t a city with two great restaurants and tourist traps. This is a city where the breakfast sandwich shop sources pastured pork, where the diner uses day-boat fish, where the donut shop mills Maine potatoes into dough.

You’ll eat better here than in cities five times the size. You’ll talk to chefs about their ingredients. You’ll taste oysters pulled from water you can see from your table.

A weekend in Portland isn’t long enough. But it’s enough to understand why chefs move here, why food writers obsess over this city, and why locals will argue passionately about which restaurant makes the best lobster roll.

Come hungry. Leave planning your next trip back.