Things to do in Portland
And where to stay, the best time to visit, what a day costs, and the traps to skip.
Best time to visit Portland
• a note or something on ✦ an occasion worth the trip
Spring is mud then openings. March is still winter, April is quiet and cheap, late May is a sweet spot as sights reopen.
Summer is the full city at full price. Late June is the insider pick, July and August are busiest with cruise days and sold out rooms.
Fall is the best weeks of the year. September is finest, foliage peaks around early to mid October, and the season ends after Indigenous Peoples' Day.
Winter is cheap, cosy and dark early. Best for the indoor city, Christmas dressing and light displays, with shacks and most boats closed.
What's on
- Maine Restaurant Week early March
Prix fixe across the city, the best value eating week of the year.
- Pride Portland June
Pride celebrations in Portland in June, during the full summer season.
- Yarmouth Clam Festival third weekend of July
Clam festival in Yarmouth, an easy trip from Portland in peak summer.
- Maine Lobster Festival early August
Rockland's lobster festival, about 1.5 hours from Portland.
- Harvest on the Harbor Usually mid October
Food festival with the Maine Lobster Chef of the Year competition and Maine OysterFest.
- Gardens Aglow late November-December
Walk-through light display at Coastal Maine Botanical Gardens that draws the whole state and sells out.
- Victoria Mansion at Christmas late November-December
Separately ticketed Christmas dressing of the house, treated by locals as an event in itself.
- Christmas Prelude early December
Kennebunkport's two weekend Christmas festival, the one winter day trip worth timing.
Best things to do in Portland
Old Port
Walk Commercial Street and the working wharves first, then loop back through Exchange and Middle for shops.
Portland Head Light
Maine's oldest lighthouse in Fort Williams Park, with cliff paths, fort ruins and the classic harbour entrance view.
Casco Bay Lines
Working ferries to Peaks Island and the Mailboat Run, so the bay crossing feels like real Portland transport.
Portland Museum of Art
Maine's largest art museum, strong on Homer, Hartley, Nevelson and the Wyeths, and doable properly in two hours.
Portland Observatory
The last maritime signal tower in America, with 104 steps to the best orientation view in the city.
Eastern Promenade
Olmsted era hillside park and trail wrapping the east end, with East End Beach and sunset over the islands.
Victoria Mansion
An 1858 Italianate villa where over 90 percent of the interiors are original, including Guidicini's painted rooms.
Allagash Brewing Company
The Belgian style pioneer behind Allagash White and Curieux, with ticketed Cellars tours and a beer garden.
Where to stay in Portland
Old Port
first trip, all-round base
Densest restaurants, the ferry terminal and cobbled streets, all walkable without a car.
West End / Arts District
couples, repeat visitors, quieter stays
Victorian streets and Western Promenade sunsets, a 10 to 15 minute downhill walk to the Old Port.
East End / Munjoy Hill
food-first travellers, local-feeling stays
Washington Avenue restaurants, the Eastern Promenade and sunrise over the islands, with almost no hotels.
East Bayside
beer trips and groups
Brewery cluster and lower rates a 10 minute walk from the Old Port. Check the exact address before booking.
South Portland / Cape Elizabeth
travellers with a car, beaches and lighthouse mornings
Willard Beach, Fort Williams and Crescent Beach on your side of the water, with lower rates and free parking.
Think twice about
- Airport / Maine Mall corridor
Chain motels on multi-lane roads with nothing to walk to at night and a drive and parking bill to every meal.
- Scarborough, Westbrook or Gorham motel strips sold as Portland
Listings off the peninsula and off the South Portland beach side are not staying in Portland in any sense that matters.
Best restaurants in Portland
Fore Street
The 1996 institution built around an open wood hearth, with a daily menu from Maine farms and boats.
Twelve
Seasonal prix fixe in a rebuilt 1890s Thames Street building, plus a bar lobster roll in a house croissant.
Eventide Oyster Co.
Oyster bar with a dozen plus Maine varieties and the award-winning brown butter lobster roll on a bao bun.
Central Provisions
Inventive small plates built for sharing, from bone marrow toast to suckling pig, with a bar downstairs.
Scales
A big handsome fish house on the working wharf, the one big seafood dinner slot for groups and occasions.
Duckfat
Tiny cafe built on Belgian style fries cooked in duck fat, plus duck confit poutine, panini and shakes.
Bite Into Maine
Order the flight of mini lobster rolls in Maine, Connecticut and spiced styles and settle the argument yourselves.
The Highroller Lobster Co.
Retro diner room on Exchange Street with a lobster roll flight and a lobster cheese crisp taco.
Outdoor things to do in Portland
Portland Paddle
Guided sea kayak trips from East End Beach to Fort Gorges, with a sunset version people write home about.
Lucky Catch Cruises
Ninety minutes hauling lobster traps on a working boat, measuring and banding keepers on Casco Bay.
Portland Schooner Co.
Two hour day and sunset sails on restored 1900s schooners Wendameen and Bagheera out of Maine State Pier.
Peaks Island
Ferry over and ride the flat four mile perimeter road past open ocean, Battery Steele and the village beach.
Riverside Golf Course
Portland's own municipal golf on the Presumpscot River, becoming ski, snowshoe and sledding ground in winter.
Nonesuch River Golf Club
An 18 hole par 70 public course through woods and river frontage, the sensible mid tier round near Portland.
Cape Arundel Golf Club
Walter Travis's 1921 pilgrimage course, short and strategic with fierce greens on the Kennebunk River.
Crescent Beach State Park
A mile of proper sand with gentle surf and a picnic grove, the family default beach near Portland.
Best hotels in Portland
The Press Hotel
Former Press Herald headquarters rebuilt as a design hotel at Congress and Exchange, arguably the best pin in the city.
Portland Harbor Hotel
The Old Port luxury pick on Fore Street, with nautical rooms and a garden courtyard escape from the crowds.
Portland Regency Hotel & Spa
The 1895 armory on Milk Street whose full service spa makes it the girlfriend getaway and bachelorette base.
Canopy by Hilton Portland Waterfront
New build mid range hotel at the Old Port's eastern edge with the Luna Rooftop bar and harbour view rooms.
AC Hotel Portland Downtown-Waterfront
Modern chain hotel near the ferry and East End, part of the best value central sleep cluster in local guides.
Cambria Hotel Portland Downtown Old Port
New build hotel with the ALTO rooftop terrace and harbour view rooms at the Old Port's eastern edge.
Hyatt Place Portland-Old Port
Practical mid range on Fore Street with large rooms, included breakfast and a rare Old Port indoor pool.
The Longfellow Hotel
High design independent hotel on Congress Street with the Astraea spa, arguing for best in the city.
Is Portland expensive? What a day costs
| Budget | $150 a person |
|---|---|
| Classic | $325 a person |
| Splurge | $600 a person |
A day of food, drink, sights and getting around, before the room
What to book ahead
- Victoria Mansion: a few days ahead
- Allagash Brewing Company: weeks ahead
- Portland Paddle: weeks ahead
- Lucky Catch Cruises: a few days ahead
- Portland Schooner Co.: weeks ahead
- Peaks Island: a few days ahead
- Coastal Maine Botanical Gardens: weeks ahead
- Fore Street: months ahead
- Fore Street reservations open about two months out and prime times go.
- Twelve, Scales, Chaval and Miyake fill summer weekends weeks ahead.
- Book Allagash Cellars tours, sunset paddles and sails, Peaks golf carts, Homer Studio tours and Botanical Gardens tickets when you book the hotel.
- Lucky Catch and food tour slots go on summer weekends, a few days ahead is usually enough outside August.
Is Portland safe?
- Portland is generally safe and the Old Port at night is busy and lit. Violent crime against visitors is rare.
- A visible street population gathers around the Bayside and Preble Street services corridor and around Congress Street and Monument Square.
- Stay off private working piers. Harbour water is dangerously cold in every month.
- Winter hill sidewalks ice over. Wear boots from December to March.
Portland travel tips: tourist traps to skip
- DiMillo's On the Water is the famous floating dining room locals steer you past. Spend the dinner money at Scales instead.
- The Commercial Street deck strip at midday on a cruise day is tourist priced. The same harbour is better at breakfast or dusk.
- Freeport outlets are interchangeable with anywhere. Build the day around Wolfe's Neck and Maine Beer Company instead.
- Driving to Portland Head Light at noon in August means circling for parking. Go early, late, or by bus or bike.
Getting around Portland: public transport and more
- Walk the peninsula: Old Port to the museum is 10 minutes and to the Eastern Promenade 20.
- You do not need a car on the peninsula. Rent one only for excursion days and dodge hotel parking the rest of the trip.
- Casco Bay Lines ferries run year-round to Peaks Island. Arrive 15 minutes ahead on summer weekends.
- Portland airport is 15 minutes from the Old Port. The Amtrak Downeaster from Boston takes about 2.5 hours.
Who Portland suits
| Solo travellers | Good |
|---|---|
| Groups of friends | Great |
| Couples | Great |
| Bachelor parties | Great |
| Families | Good |
| Bachelorette parties | Great |
Make Portland your trip
Swearby drafts the days from places people swear by. Swap any stop, then invite the crew by text, even friends without the app. Vote on dates, track costs as you go, and everyone gets one number at the end.
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