Road trip through Coastal Maine

For our Maine summer weekend roadtrips we are always looking for best views and lobsters.  Here is our 3-day Coastal Maine Itinerary (aka lobster crawl) as told in LOBSTER stops.  We did this trip over a (long) weekend (2 nights, 3 days) but you could of course extend any part of the trip and easily spend a week road tripping through the Maine coast.

Coastal Main Roadtrip
Our 3-day Coastal Maine roadtrip

You could also follow our Maine roadtrip on our youtube channel.


We started the roadtrip at our home south of Boston and our first stop was at 2-hour point in Kennebunkport, Maine.  This scenic coastal town with lively Main street was a mid-way stop to our destination in Southport Island, Maine.

Kennebunk river, Main Street, Kennebunkport, Maine

Before we indulged in seafood delicacies we stopped at the Colony Beach by the historic namesake hotel to get a first glimpse of Maine’s rocky coast on this trip.  We also took a quick coastal drive along the Ocean drive towards the Walker’s Point – to take in more of the rocky coastal scenery and to “peep” over the channel onto the President Bush’s family compound.  (There is a limited 15-min parking lot here for a quick stop).  The Bush family has used their Maine property as a summer getaway for more than a century!

Coastal Maine roadtrip
Ocean Drive, Kennebunkport, Maine

Views: This landmark  summer shack and fish market is located on the bridge over Kennebunk river in the center of town with atmospheric if not entirely panoramic water views.

Clam Shack, Kennebunkport

There are lots of picnic style tables, the staff is accommodating and atmosphere is lively. Once you order your food, you can take your table and enjoy your drink while waiting for your order.

Lobster Roll: Served cold, the lobster meat (mostly tail meat!) was plentiful and flavorful but we found the bun (burger style) to be lacking butter and grilling (of course we only realized that having tried 4 other rolls on this trip).

Extras: Fried Clams were the best we’ve had all summer; beer and wine are available for order.


I found the Southport Island by chance when looking for a hotel base near Boothbay Harbor for our 3 day coastal Maine roadtrip.  This  “hidden” Maine treasure will surely draw us back.  Lacking in touristic bustle of the nearby Boothbay Harbor it offers a simple and serene coastal charm.  It also made a perfect sense as our trip base.  We enjoyed the calm and natural beauty it offered and the proximity to Boothbay Harbor – for boat trips to Monhegan Island and other excursions or a busy nightlife (have we so desired).

Newagen Inn, Southport Island, Maine

Newagen Seaside Inn where we stayed is located at Cape Newagen, historic fishing village at the tip of Southport Island. We enjoyed al fresco dining at our ocean views balcony, walks to the picturesque Newagen Harbor right off the property harbor and a sunset over the rocky coast.

Sunset on Southport.

On our way home we also stopped at Southport’s Hendricks Head Beach to take a look at the Hendrick Head historic Light House (built in 1870) at the mouth of the Sheepscot River.

Hendrick’s Beach, Southport, Maine

Views: We sat on a lovely terrace overlooking hotel grounds with Newagen Harbor as the backdrop.

Lobster Roll: was served warm on a perfectly buttered and grilled bun and was not lacking in quality, but possibly needed a bit more quantity of the meat.

Extras: mixed drinks and interesting menu in this full service, full menu restaurant are a draw


Monhegan Island was an inspiration behind this coastal Maine roadtrip itinerary.  We were intrigued by the island’s remoteness (14 miles off the coast) and rugged beauty and considered spending the night there -although not prepared to hike its hilly around the island trails.  Staying overnight did not prove possible logistically (given the limited number of commercial boat options and the limited time we had on this trip. We settled on a half day Balmy Days cruise from Boothbay Harbor that gave us just under 4 hours on the island.

In this time we managed to visit several stops of the Arts Walks (many of the town’s residents are artists), explore the Village, taste local beer (and of course lobster), go on a 30-minute hike to Lobster Cove, circle the island on a boat and even shop for souvenirs (books on the history of the island).

There are several ways to get to this small island (less than a mile in width and less than 2 miles in length, with about 65 year-round residents) – all of these require a boat (typically in the morning) from several Maine locations (Boothbay Harbor was the shortest distance from Boston) but others (Rockland and Port Clyde) may work better with your Maine itinerary.


Views: this casual eatery with picnic tables right by the turquoise waters of the Monhegan Harbor overlooking the Manana Island were the best views of all 5 lobster pits we surveyed on this trip (if you can’t grab a spot on one of the two tables by the water – there is an adjacent sandy beach as a backup seating plan).

Lobster Roll: served cold and not particularly impressive in the amount of meat, it won me with a perfect combination of mayo and butter- a formula which quite possibly brought me closer to uncovering a secret to a perfect lobster roll!

Extras: soups (clam chowder and lobster bisque) were tasty too and this small shack (and fish market) offered some innovative salads.


Nicknamed “the prettiest village in Maine”, historic Wiscasset is located on the Sheepscot river (and on US route 1- most likely you will pass it it on your way from Boston/Portland to Boothbay Harbor).  It took us only 30 minutes from our hotel on Southport Island to reach Wiscasset on the final morning of our trip.  After our morning walk and swim on Newagen, we decided to have a lobster lunch at the town’s famous Red’s Eats – notorious for its lobster roll (and long lines).  Even during the “quieter” summer of 2020, our wait for Red’s lobsters was close to 2 hours! It was our anniversary and Vit generously offered to stay in line while I explored the shops and galleries on Main street. We did not check out the town’s 19th century architecture on this trip but it is something we plan to do on future trips.


Views: the state’s best known lobster shack is overlooking Sheepscot River but it is also next to a busy road (US 1) which diminishes the “views” factor.

Lobster Roll at Red’s Eats

Lobster Roll: is Huge and flavorful; the family takes pride in each and every roll they serve and it shows.  You are given the sides of  mayo and butter to mix by yourself and while the Kate’s butter is very nice, the brand of mayo that they serve is not the one I am used to (brought up in Soviet Unio I am no stranger to heavily mayo-ed salads) and it took away from my “Red’s” lobster experience.

Extras: fried scallops are fresh and they served sides of local tomatoes.

Note: be prepared for 1-2 hour lines. They serve you water and even small bites while you wait but it is still not fun by no means.


When I plan our roadtrips, I typically choose the stops for its natural beauty and/or historic and cultural significance (or some other more quirky reasons), but I also try to make sure they make logistical sense. Two Lights State Park on Cape Elizabeth was our last stop on this trip before heading home- and it was perfectly situated at a 2-hour drive point from home.    We also considered possibly stopping in East Point Sanctuary in Biddleford Pool but having spent two extra hours in traffic near Portland- have simply ran out of time.

“Ancient amphitheater” like coastal stone formations at Two Lights Park

Two Lights impressed us with its paved coastal trail along the rocky coast lined with unusual stone formations.  The stones were flat and formed theater like amphitheaters filled with people and chairs (we saw several couples playing chess).

The two lighthouses that gave the park its name are actually located outside the park (at the end of Two Lights Road) and are not accessible to the public (the eastern light is still active and visible at sea; the western light is a now a private residence).  The picnic tables with views over the ocean are available (and are nicely enclaved by surrounding bushes).


Views: This shack is adjacent to the Two Lights Park and shares its coastal views (you can possibly hike from the Park- we did not).


Lobster Shack, Cape Elizabeth

Lobster Roll: Compared to the others on this trip, this roll was just OK, tasty but smallish, and no butter offered on the sideTip: call ahead for your order to (practically) eliminate the wait.

Start planning your coastal Maine roadtrip!  Here is another story to inspire you – this time a FAMILY WEEKEND IN COASTAL MAINE.


For one of our recent couple’s coastal Maine weekends we did not make any “ahead” plans but were happy to discover Cabbage Island Clambake in Boothbay Harbor! This event (run during the summer) sells out weeks in advance (follow link above to reserve) but we showed up in the morning, got on the wait list and were given coveted tickets when we showed up again at 12:15 for 12:30 excursion (there are typically 2 trips on each weekend day).

We loved everything about this “unplanned” lobster experience: picturesque narrated trip to the island, walks to the gorgeous “corners” of the little island, watching the food being atmospherically prepared in front of us right next to the ocean, the food itself, the service, the atmosphere- we will be back!

Views: picnic tables were all over, and you could see the water from all spots as you enjoyed your feast.

Lobster: steamed with seaweed next to the ocean, these were the most tender and flavorful lobsters we have ever had (and we had our share!)

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Coastal Maine Road trip


6 thoughts on “Road trip through Coastal Maine”

  1. Dear Victoria, Thank you for the inspiration! As always you provided great tips! We loved Kennebunkport and the costal trip. It was amazing!

    1. Victoria@celebratetheweekend

      Great to hear from you, Jane! I am glad you enjoyed your coastal Maine getaway! thanks for stopping by!

  2. Huge mistake going to Reds Eats in Wiscasset. You should have gone across the street to Spragues. A true water front and the lobster is fresh and not shipped in in from Canada. Ate there once and the lobster had ice in it. Will never go there again.

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