Dining Guide · Maine · Vermont

Portland, Maine

May 22–26 · 4 nights

One of the best food cities in New England — remarkable concentration of excellent restaurants for its size. The Old Port district and surrounding neighborhoods run deep with raw bars, wood-fired kitchens, and creative cooking. Staying with friends means complete flexibility to explore at your own pace.

Restaurants & Bars

Eventide Oyster Co.

★

Seafood Raw Bar

One of the most celebrated oyster bars in the country — a Portland landmark. Rotating raw bar selection of bivalves plus creative cooked preparations. The brown butter lobster roll on a steamed bun is the signature; order it. Do not miss.

Reservations recommended · Popular — walk-in waits are common

Fore Street

★

Wood-Fired American

The restaurant that put Portland on the national map. Sam Hayward's open-hearth kitchen has been defining Maine cooking since 1996. Signature dishes: spit-roasted pork loin, wood-grilled mussels, whole roasted garlic. A serious institution and a genuine destination meal.

Reservations essential · A Portland must

Central Provisions

Small Plates American

Inventive small-plates restaurant in the heart of the Old Port. Chris Gould's globally-influenced cooking — one of Portland's most consistently excellent spots for a longer, exploratory dinner with good drinks to match.

Reservations recommended

Honey Paw

Noodles Asian-Influenced Veg-Friendly

Below Eventide (same owners). Creative, globally-influenced noodle dishes — menu rotates with seasonal Asian-inspired preparations. Excellent vegetarian options alongside meat dishes. Lively, casual atmosphere — a great complement or alternative to Eventide upstairs.

Walk-ins often possible · Shares team with Eventide

Duckfat

Casual Lunch

Famous for Belgian-style fries cooked in duck fat — deeply crisp, richly flavored, and worth seeking out. Excellent panini and casual fare. A Portland institution. Perfect for a relaxed midday meal or a quick early stop before a longer evening.

Walk-in · Lunch and early dinner

Stowe, Vermont

May 26 · Drive-day lunch stop

A natural lunch stop on the drive from Portland to Burlington — just before Smugglers' Notch pass. The food scene exceeds expectations for a ski town; worth pausing properly rather than rushing through.

Lunch Stops

Hen of the Wood

★

Farm-to-Table Vermont Veg-Friendly

One of Vermont's most celebrated restaurants — Stowe location (also in Burlington). Hyper-seasonal menu driven by local farms, exceptional vegetable preparations, beautifully sourced meat and fish. Worth stopping for a proper sit-down meal on the drive day.

Reservations recommended · Also has Burlington location (May 27)

Harrison's Restaurant & Bar

American Casual

Reliable, well-regarded Stowe staple on the main street. Solid American cooking — a comfortable, unfussy option for a relaxed lunch before tackling Smugglers' Notch in the afternoon.

Walk-in friendly for lunch

Butler's Pantry

Café Light Lunch

Easy, low-key café stop in Stowe. Good for lighter fare — sandwiches, salads — when you want a quick break before continuing through the pass to Burlington.

Walk-in · Lighter fare · Quick stop

Burlington, Vermont

May 26–28 · 2 nights · Hotel Vermont

Burlington punches well above its weight for a city of 45,000. It has one of the most active US Bartenders Guild chapters in the country — even incidental restaurant bars tend to be above average. A focused, high-quality dining scene anchored by local sourcing and genuine craft.

Restaurants

Honey Road

★

Eastern Mediterranean Vegetarian Paradise

The top restaurant pick in Burlington. Chef Cara Chigazola Tobin's Eastern Mediterranean mezze restaurant — one of the best in Vermont. Exceptional small plates: hummus, kibbeh, lamb, roasted vegetables, all with real depth of flavor. Great cocktail program. A meal here is a highlight of the Burlington leg.

Reservations strongly recommended · Church Street area

Hen of the Wood

★

Farm-to-Table Vermont Veg-Friendly

Flagship Burlington location of one of Vermont's most acclaimed restaurants. Hyper-seasonal, ingredient-driven cooking — exceptional vegetable preparations alongside beautifully sourced meat and fish. Rustic-elegant space, intimate and warm.

✓ Reservation confirmed: Wed, May 27 · 7:30 PM

Frankie's

American Cocktails

Solid dinner with an acclaimed cocktail program. Bar Manager Max Pogacar is known for clarified milk punches and creative seasonal drinks that rival dedicated cocktail bars. A reliable, convivial choice for a Burlington evening out.

Walk-in or reservations

Cocktail Bars

The 126

★

Cocktails Speakeasy Live Jazz

The top craft cocktail destination in Burlington. Hidden behind a deli door on College Street — a cozy speakeasy with live jazz that's never too loud. Consistently the best cocktail bar in the city. Small, intimate, and seriously accomplished drinks program. Don't miss it.

Find the deli door on College Street · Jazz most evenings

Paradiso Hi-Fi

Vinyl Bar Cocktails

Vinyl listening bar with excellent cocktails and snacks. A good late-evening stop with a relaxed, music-forward atmosphere — curated record selections and thoughtful drinks in an intimate space. Perfect for winding down after dinner.

Good for late evening · After-dinner option

Devil Takes a Holiday

Cocktails Speakeasy

Speakeasy-style cocktail bar with a mix of classics and creative twists. A moody, intimate space with a strong program — solid Burlington option if The 126 is full or you want a second stop.

Walk-in

BKK in the Alley

Cocktails Thai-Influenced

Thai-influenced cocktail program tucked down an alley near Church Street. Distinctive flavor profiles — lemongrass, galangal, makrut lime — in a compact and energetic space. A uniquely Burlington experience.

Walk-in · Alley near Church Street

Hotel Vermont Bar

Cocktails Hotel Bar

The bar at your hotel. Polished, well-executed program in a handsome space — better than most hotel bars by a wide margin. Jazz on Wednesday evenings. An easy and excellent option when you don't want to go far after a full day.

Jazz Wednesdays · 41 Cherry Street · In your hotel

Montréal, Québec

May 28 – June 1 · 4 nights · Hotel Gault

One of the great food and drink cities in North America. The cocktail scene is world-class — two bars consistently ranked among the continent's best. The restaurant scene ranges from Syrian fine dining to all-vegan sushi, creative bistros, and woodfire kitchens. Book Mon Lapin and Cloakroom Bar well before you arrive.

Restaurants

Restaurant Candide

✓

French Seasonal Veg-Friendly

Intimate seasonal bistro in the Plateau-Mont-Royal. Market-driven French cooking with a focus on Québec producers — tight, carefully composed menus that change with what's available. Precise, unfussy dishes with genuine depth. One of Montréal's most quietly acclaimed neighbourhood restaurants.

✓ Confirmed Reservation · Thursday, May 28 · 6:30 PM

Mon Lapin

★

Small Plates Natural Wine Veg-Friendly

Frequently ranked the #1 restaurant in Canada. Inventive, constantly evolving small plates with exceptional vegetable dishes. Outstanding natural wine program. Part of the Joe Beef group — same energy and excellence, but lighter and more playful than its sibling. A genuine must. Reserve well in advance.

Reserve well in advance — one of the city's most sought-after tables

Damas

★

Syrian Fine Dining Veg-Friendly

Syrian fine dining in Outremont. A gorgeous room with exceptional cooking — mezze, kibbeh, lamb and aubergine preparations drawn from the best of Syrian culinary tradition. Many outstanding vegetarian dishes. One of Montréal's most beloved restaurants. Damas or Larrys are both recommended for the arrival evening.

Reservations recommended · Outremont · Good arrival-night option

Hoogan et Beaufort

★

Wood-Fired Seasonal

Hyper-seasonal woodfire grill in a converted industrial warehouse. One of the best wine lists in Montréal. Beautifully executed fire-cooked dishes with a strong emphasis on local Québec ingredients. Dramatic, open space — a big, satisfying evening.

Reservations recommended

Larrys

Bistro Brunch & Dinner

Creative neighborhood bistro in the Plateau–Mile End area. Casual but genuinely exceptional — the kind of place Montréal does effortlessly well. Good for brunch or a relaxed dinner. A natural choice for the arrival evening alongside Damas.

Walk-in friendly · Plateau · Good arrival-night option

Vin Papillon

Small Plates Natural Wine Veg-Forward

The vegetable-forward wine bar from the Joe Beef group. No reservations — arrive at opening or expect to wait. Creative, ingredient-driven small plates with an outstanding natural wine selection. A very Montréal experience: smart, unpretentious, and delicious.

No reservations — arrive at opening · Walk-in only

Le Petit Alep

Syrian & Armenian Veg-Friendly

Family-run Syrian and Armenian restaurant with an exceptional mazza spread. Levantine spices done with care and authenticity — and one of the best wine lists in the city, thoughtfully curated to match the cuisine. A Montréal gem that rewards discovery.

Reservations recommended

Sushi Momo

Sushi All Vegan

All-vegan sushi — shockingly creative. Non-veg diners consistently love it. Beautifully executed plant-based interpretations that stand on their own rather than simply mimicking. A genuinely surprising meal in a city full of surprises.

Reservations recommended

Cadet

Casual Market-Forward Veg-Friendly

Casual, market-driven cooking with fresh, seasonal ingredients. A great option for a lower-key but well-executed meal — the kind of neighborhood restaurant that makes Montréal such a formidable food city across every price point and register.

Walk-in friendly

Cocktail Bars

Cloakroom Bar

★

Cocktails No Printed Menu

#2 in Canada and #31 in North America (50 Best Bars 2025). Twenty-five seats — no printed menu. Bartenders craft personalized cocktails using rare and vintage spirits based on what you tell them you enjoy. The most serious, personalized cocktail experience in the city. The kind of bar you talk about for years.

Reservations strongly recommended · Golden Square Mile

Atwater Cocktail Club

★

Cocktails Walk-In Only

Altos Bartenders' Bartender Award 2024 winner — the award given by bartenders to the bar they'd most want to drink at. A graffiti-lined alleyway entrance leads to one of the best cocktail bars in the country. Walk-ins only. A destination in its own right.

Walk-ins only — no reservations · Hidden alleyway entrance

Foxy

Cocktails Michelin Award

Michelin Exceptional Cocktails Award winner — the only bar in Montréal with that distinction. A well-crafted program in a stylish space. Worth visiting on the strength of the accolade and the quality of the work behind the bar.

Reservations possible

The Coldroom

Cocktails Speakeasy

A speakeasy in a 19th-century cold storage cellar in Old Montréal. Look for the unmarked black door with a duck logo. Low ceilings, stone walls, and seriously good cocktails in one of the most atmospheric rooms in the city. Walking distance from Hotel Gault.

Unmarked black door · Duck logo · Old Montréal · Near Hotel Gault

Le Mal Nécessaire

Tiki Cocktails

Tiki-inspired bar with plush velvet banquettes and cocktails served in hollowed-out fruit. Best of MTL 2025. A more playful, theatrical evening — genuinely delicious drinks in an over-the-top setting. A good contrast to the more austere precision of Cloakroom.

Walk-in · Chinatown area

Big in Japan

Whisky Bourbon

Whisky and bourbon focus in an intimate, candlelit atmosphere. An excellent selection of Japanese and American whiskies. A quieter, more contemplative late-night option after dinner — good if you want something calmer than the cocktail bar circuit.

Walk-in · Late night