Boston Escape: Road Tripping to Quaint Poland, Maine

Are you destined to quaint Poland, Maine? Plan a Boston to Maine road trip for a delightful adventure exploring coastal New England’s main streets and back roads. Escape the city for a leisurely drive up the coast, stopping to discover the picturesque cities and towns that line the Atlantic seaboard.

Or, take the more direct route to the Maine Turnpike, getting off in Gary for a quick visit to the Maine Wildlife Park and a peaceful hike through the Libby Hill Forest Trails. Either route takes you to our little slice of heaven on Tripp Lake in Poland, Maine.


— Take the Leisurely Route —

Scenic Driving Directions

  1.  Hop on I-95 North to the Maine Turnpike
  2.  Exit I-95 at Exit 3 to Portsmouth, NH (pit stop)
  3.  Follow US-1 from Portsmouth, NH, to Kittery, ME (pit stop)
  4. Get back on 1-95 North
  5.  Take Exit 25 Fletcher St. to Kennebunk, ME (pit stop)
  6. Jump back on 1-95 North
  7. Take Exit 4 into Portland, ME (pit stop)
  8.  Follow ME-26 North and merge onto I-95 North/Maine Turnpike
  9. Take Exit 63 to Gray, Maine
  10. Turn Right onto ME-26
  11. Turn Left onto North Raymond Rd
  12.  Turn Right onto ME-11
  13. Turn a slight Left onto Jordan Shore Dr.
  14. You’ve arrived!


Favorite Pit Stops Along the Way

——Portsmouth, NH

This city exudes a vibe of coastal maritime history and modern charm on the Piscataqua River. Wander the picturesque streets of downtown Portsmouth, filled with lovely boutiques, intimate bistros, and enchanting art galleries.

Stroll along the waterfront and visit historic points of interest. Portsmouth, a small but vibrant city with a lively cultural scene and a long connection to its nautical heritage, captivates all who visit.

Our Recommendations:

  • Strawbery Banke Museum: A 10-acre outdoor history museum featuring restored houses, exhibits, and gardens
  • Prescott Park: A beautiful waterfront park with gardens and picnic areas, and often hosts outdoor concerts and festivals
  • Our Favorite Restaurant: The Black Trumpet Bistro offers a cozy, waterfront dining experience with a seasonal menu that highlights local ingredients

Additional Places to Eat:

  • River House
  • Row 34
  • Caffe Kilim
  • Cava
  • Cure
  • Earth Eagle Brewing

Additional Things to Do:


——Kittery, ME

Known as an outlet shopping mecca, Kittery maintains an aura of coastal charm primarily in its downtown area, Kittery Foreside. A recent transformation has revealed a colorful collection of trendy boutiques, craft coffee shops, and chef-owned and operated restaurants.

Kittery is the oldest incorporated city in Maine and home to the Portsmouth Naval Shipyard, the nation’s longest-serving Navy yard. It blends its maritime history with the upbeat vibe of a thriving coastal village.

Our Recommendations:

  • Kittery Trading Post: A must-visit for outdoor enthusiasts, offering a wide range of gear and clothing
  • Kittery Outlets: Great for shopping with a variety of brand-name outlets
  •  Favorite Coffee Shop: Lil’s Café is a popular spot for delicious pastries and coffee

Additional Places to Eat:

  • Roberts Maine Grill
  • Tulsi Indian Restaurant
  • Ore Nells
  • Anneke Jans
  • When Pigs Fly
  • Beach Pea Baking
  • Anju Noodle Bar
  • Loco Coco

Additional Things to Do:


——Kennebunk and Kennebunkport, ME

Two of Maine’s favorite coastal destinations, Kennebunk and neighboring Kennebunkport, owe much of their fame to former president Bush, a noteworthy summer resident. A drive along Ocean Avenue takes you right by the entrance to the gorgeous waterfront estate.

Kennebunk attracts visitors from all over with its charming shops and elegant eateries. When downtown gets busy, wander north along the shore to Cape Porpoise and Goose Rocks Beach for peace and quiet.

Our Recommendations:

  • Kennebunk Beaches: Beautiful, sandy beaches perfect for a relaxing stroll
  • The Brick Store Museum: A local history museum with interesting exhibits
  • Our Favorite Restaurant: The White Barn Inn Restaurant offers fine dining with exquisite New England cuisine in a charming barn setting. Actually, it’s really a toss-up between the White Barn and the elegant Earth at Hidden Pond.
    • The 4-course dining experience we had was unforgettable. We had venison and duck and they were mouth-watering delicious! Dessert was simple, yet beautifully displayed doughnuts. Amazing! Of course, this place has a little sentimental value as well because we had just found out that Nicole was pregnant with Aiden, our little “wolf cub.”

Additional Places to Eat:

  • Boulangerie
  • The White Barn Inn
  • Hb Provisions
  • Bandaloop
  • Lobster Roll Trail of the Kennebunk
  • Chef Rosas
  • The Boathouse

Additional Things to Do:

  • Beaches: Colony, Parsons, and Mothers
  • Museum in the Streets
  • Landmark Gallery
  • Northlight Gallery
  • Chris Becker Photo Gallery
  • Sue Roux Designs
  • Dock Square Emporium
  • Gooch’s Beach
  • Ganny’s Garden
A view from the docking area of the red brick buildings of Portland, Maine

——Portland, ME

The city of Portland blends a metro hub with the charming cobbled streets of the Old Port district. Spend the day exploring the working seaport area, take a ferry to one of Casco Bay’s offshore islands, or take a self-guided walking tour through this genuinely stylish and sophisticated metropolis.

Lighthouses and lobsters form the framework of Portland’s most anticipated treasures. But with a heady mixture of art and adventure, a visit to Portland satisfies all the senses.

Our Recommendations:

  • Old Port: A historic area with cobblestone streets, boutiques, and restaurants
  • Portland Head Light: An iconic lighthouse with stunning views
  • Our Favorite Restaurant: Fore Street is known for its wood-fired cooking and emphasis on local ingredients.
    • This restaurant speaks my food love language. The service was incredible, and I could eat their Wood-Grilled Hangar Steak every day. They also partner with some of our own farmer/growing partners at Wolf Cove Inn! Nicole and I ate here for my birthday last year with my mom and stepdad, just a few weeks after Aiden was born.

Additional Places to Eat:

  • Portland Lobster Company
  • Butcher Burger
  • Via Vecchia
  • Papi
  • Henry’s Public House
  • Saltwater Grille
  • Paper Tiger
  • Harbor Bistro and Terrace
  • Gross Confection Bar
  • Alto
  • Rigby Yard
  • The Grill Room
  • North 43 Bistro

Additional Things to Do:

car driving on a highway toward the rising sun

— The Quick Route —

Fastest Driving Directions

  1. Hop on I-95 north to the Maine Turnpike
  2. Take Exit 63 towards Gray, Maine (pit stop)
  3. Turn Right onto ME-26
  4. Turn Left onto N Raymond Rd
  5. Turn Right onto ME-11
  6. Turn a slight Left onto Jordan Shore Dr.
  7. You’ve arrived!


Favorite Pit Stops Along the Way

——Gray, ME

This quintessential New England town is between Portland and Freeport in southern Maine. Known for its abundance of recreational activity, the Maine Wildlife Park is here. The park protects injured or orphaned wildlife.

Libby Hill Forest, another Gray, ME landmark, offers miles of groomed hiking and cross-country skiing trails. Blessed with lakes, a great golf course, and quaint antique shops, Gray makes a great stop en route to Wolf Cove Inn.

Our Recommendations:

A plate of oysters and lemon slices

Where to Eat Along the Way

Every great road trip includes an opportunity to sample the region’s culinary delights. Lobster, of course, tops the list of treats found in Maine. Mastering the art of deconstructing a whole lobster is not for the faint of heart. It’s a science carefully studied by all lobster lovers.

However, many dining establishments offer dozens of ways to appreciate this delicacy. So, to find the best places to eat lobster in Maine, let us introduce you to a few of our favorites.

In addition to lobster and the finest fresh seafood, Maine offers a wealth of great restaurants. Several excellent restaurants stand out in and around Poland. But for our road trip, let’s break it down town by town.

What to Do Along the Way

Each of our favorite pit stops on a road trip to quaint Poland, Maine, offers fun, funky, and entertaining activities. See our linked lists above! However, once you reach Wolf Cove Inn, we recommend many great ways to explore the area. But each of these road trip pit stops deserves a bit of time to get to know better.

The Ultimate Boston Escape

So, the next time you need an escape, plan a Boston to Maine road trip. The sights, sounds, and smells along the way will lead you to tranquil luxury at Wolf Cove Inn in Poland, Maine.

We welcome you to our charming and relaxing lakeside retreat, an oasis in the heart of the lakes district.

Published April 2024

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