The first stop on our New England road trip was the furthest way ~ the great state of Maine! It was my first time in Maine, and I was eager to explore The Pine State, but let’s be honest.. mostly eager for some Maine lobster rolls! We stayed in Kennebunkport and ventured to the fun & funky towns of Portland and Ogunquit, both of which are definitely worth checking out! Maine is the quintessential New England experience and such a perfect (and easy!) escape from New York City!
The Town of Kennebunk port is nestled 40-minutes south of Portland and 15-minutes north of Ogunquit This cute little New England town has some history (founded in 1653!) and is picture-perfect. It might have been the first time I heard about KPT but I met my good friend Kit, who I met in the early days of Chicago, is the only person I know from there. The town is just under 4,000 residents – and she had the hook-up when it came to great spots to eat at in town! President George Bush’s family also has a compound that they have been vacationing at since the 70s in the summer. When they are in town, the whole city knows because they fly the Texas flag high from their prominent spot on Walker’s Point. There is so much to do in & around Kennebunkport between hiking, lobster fishing, and hitting up the coastal beaches – that I can’t wait to get back!
Kennebunkport
- The Clam Shack – A KPT staple since 1968, they’re serving up fried seafood and iconic for their lobster rolls!
- Pearl – Great New England east
- Spat – Oyster & wine bar (currently closed due to COVID-19)
- Port Lobster – Fresh lobsters straight from the fishermen, so you know their lobster rolls are a must!
- Old Vines – Great wine bar serving up small plates and great flavor
- Boathouse – One of the best-situated restaurants, right in the Harbor! Good happy hour & great New England bites!
- Pilot House – a local dive bar for a late-night drink
- Fiafia – Prime breakfast spot for great coffee, artisanal toasts, or acai bowls!
- Chez Rosa – Traditional French cuisine in a beautiful space
- Pier 77 – located in Cape Porpoise with great views of the lighthouse, this place is serving some traditional New England staples with a twist!
- Daytrip Society – Cute shopping
- Earth at Hidden Pond- Organic-inspired al fresco dining on the beautiful Hidden Pond property
- Brewed Awakenings – Cute coffee spot coming into town that is serving up donuts, ice cream, and smoothies too!
- Bitter End – On the way into town – has a cute patio that usually has live music (not currently, due to COVID-19)
- Batson River Brewing & Distilling – Great spot for cocktails & late-night drinks with a prime patio!
- The Candyman – local confections and fudge!
- Mike’s All-Day Breakfast – Great spot for breakfast or lunch with a good deck
To Do:
- Rachel Carson Nature Preserve – 7 minutes south of the town, take a hike in 14,000 acres of pristine Maine nature!
- Goose Rock’s Beach – about a 7-minute drive north of Kennebunkport, this cute beach is the perfect place to spend an afternoon! Parking is pretty tough to come by – it’s quite limited near the beach and the rest is for residents only. It’s $25/day and you have to purchase a parking permit at the Goose Rocks General Store (cash only!)
- Rugosa Lobster Boat Tour – Such a fun (& educational!) way to learn about Maine Lobsters, one of the state’s largest exports. Ask for captain Mark!
- Spaces – Bright New England inspired home goods store
- Sea Love – Hand-poured custom candles
- Seacraft Vintage – Curated Nautical Antiques and finds
While in Kennebunkport, we stayed at the Yachtsman Hotel & Marina Club, which I couldn’t recommend more. It was the perfect distance from the center of town, a 3-minute walk! Each room felt like its own bungalow, with its all-white interior and vaulted ceilings. The property is right on the water, so every room has a porch that backs-up right to the water’s edge! It also features a one-of-a-kind floating barge that they’ve converted into a luxurious pool!
Portland (40-minutes north of Kennebunkport)
- Chaval
- Fore Street
- Central Provisions
- Eventide Oyster Co. – A must! The brown butter lobster roll is served in a bao bun and truly something else.
- Hugo’s
- Rosies
- Petit Jacqueline
- Blythe and Burrows
- Island Creek Oysters
- Oxbow Brewing Co.
Ogunquit (15 minutes south of Kennebunkport)
- 360 Bar – New England bites and cocktails at Anchorage by the Sea
- The Front Porch – Lively piano bar serving up some yummy New England bites
- Leavitt Theater – Has a small and delicious menu. Great cocktails, a must!
- Bessie’s – Fantastic breakfast/brunch spot
- Loveshack Juicery – boho health food restaurant, coffee & acai bowls
- MaineStreet – LGBT Bar to catch a drag show at
I do want to note that we were here during Summer 2020, so COVID-19 precautions were in place. There was a mask mandate and the town felt very safe with everybody respecting other’s space and complying with the rules! If traveling, please be sure to check the state’s travel rules and know your status.
Also, a talented friend of mine, Gray Malin, just released a new collection of gorgeous photographs from Maine. If you’re a Mine fanatic and love to see the state from the sky, Gray’s stunning photography highlights the beauty of Maine’s 100 days of summer!
Have you been to Maine? There might be some towns with funny names there, but they sure are New England cute! I hope this guide helps you out if you’re going to Kennebunkport, Portland, or Ogunquit! I already can’t wait to get back, hopefully in the fall! Let me know if you end up making it to Maine and if you have any recommendations that I might have missed or need to do next time!
Stay Risky,
– John
Photography by Sam Waxman
