Maine – My Way

Greetings! I’m glad you found The Maine Diaries! If you want to experience the joys of New England, and specifically the coast of Maine, this is a good guide.

I started The Maine Diaries because I’ve love traveling the Maine coast and want to share my experiences with you.  They are based on my 25 road trips that started in 1994.  My traveling partner – and my partner in life – is my spouse, Joseph Eagle.

On my trips, I leave from West Chester PA (a western suburbs of Philadelphia). The destination is always the same: the area of coastal Maine known as Downeast, on Mt. Desert Island – the largest island off the coast of Maine – and home to Bar Harbor and the breathtaking Acadia National Park.

The road trip Downeast (from Philadelphia), is 10-13 hours, depending on how often you stop. I’ve done it in a one-day drive, and it’s doable. But it’s long with usually at least two traffic bottlenecks (usually in CT and MA). So if you can do an overnight along the way, do it. You’ll enjoy the ride – and the trip – more. However, if you do, don’t just stop at some no-tell-motel. Pick a place to explore and make it fun. Along the coast, there are unlimited places to have an adventure. Many of those places are mentioned, and some detailed, in The Maine Diaries.

The Drive

How I make the trip  is driving straight through PA, NJ, NY, and CT (all places close enough that I can explore another time in a weekend getaway).  Then I meander through Massachusetts, New Hampshire, and once in Maine, along the coast through southern Maine, Portland/Casco Bay, and Mid-coast to get to my Downeast destination. You can easily follow the areas on a map.

After years of trying different routes north, Joseph and I found the best – and least stressful – way is the PA Turnpike to Garden State Parkway around NYC and over the TappanZee/Cuomo Bridge, to the Merritt Parkway and I84 in CT, to I90E (Mass Turnpike), 495N (around Boston) to I95N through NH into Maine.

Side Trips and Overnights


  • Sturbridge/Walden Pond: This is where I typically stop for a meal. Old Sturbridge Village is a “living history museum” and worth seeing one time. Also along the way, as you drive east toward Boston, you could stop at Walden Pond. It’s a townie park now and, on a nice day, crowded with bathers. However, if you’re a fan of Henry David Thoreau there is a small area that would interest you. If not a fan, don’t bother.
  • Boston: You can do an overnight in Boston. but there’s so much history to see and cool things to do in the town, it’s worth a couple overnights, or a trip on its own. On my way to Maine, I like to go just a bit further north until I stop for the overnight.
  • Salem MA: This town is about 5 hours from Bar Harbor. I only stop here if I’m also doing a second overnight in Portland ME. I love a stop here, and have done it a few times. It’s a cute town – lots of witchy stuff to see. I’d pass on most of the touristy “witch trial” stuff. Three fabulous things do for an overnight, presuming you get there in mid-late afternoon:
    • The House of the Seven Gables tour. So interesting! It’s worth reading some – or all – of the book in which Hawthorne describes some of the historical buildings that still exist today.
    • Ghost Tour. There is also a ghost tour presented by a true warlock who is more focused on history than ghosts. He’s fabulous!
      • He took us past the old jail (now condos) and the Monopoly Houses (Parker Brothers games were born in Salem)
    • The Peabody Essex Museum is nice on its own, but the “don’t miss” thing to see at the PEM is the authentic Chinese house. Built in 1800 – bought in China, dismantled there and reassembled here. It’s fascinating to see and the videos of the moving process are something to see.
    • Hotels: I’ve stayed at the historic Hawthorne Hotel on a B&B deal. It was OK, pricey with tiny rooms – but worth taking a look and having a drink in the Tavern and breakfast was good. I loved the Salem Inn. When I was there it included wine and cheese at 5pm, which we enjoyed in the quaint and quiet courtyard, and breakfast. And a ghost…which Joseph and I named Catherine.
    • Marblehead: About 10″ from the town, this is a beautiful port with lots of American Revolution history
  • Cape Anne: Everybody knows Cape Cod in the south, but the northern Cape Anne is home to Rockport, with one of the most painted buildings in the country (“Motif#1”). If you go, enjoy the scenery and the seafood…but don’t miss The Paper House

New Hampshire – about 4-4.5 hours from Bar Harbor

  • Portsmouth is a cool little city. It has some history, a good nightlife, and is easy to walk. The town is very cute during the day, has some historical sections, and the couple bars are hopping – we especially like the Irish Bar.
  • The NH Liquor Store is a good stop for reasonably priced alcohol before going into Maine. It’s an easy on-off from 95. It’s much like Total Wine in DE.

Southern Maine – Lots of cute little beach towns, including…

  • Kittery. From Portsmouth or the liquor, you’re about 10 minutes from the bridge into ME – first town is Kittery. Lots of outlets but pretty much like what we have here. What is worth a stop is When Pigs Fly Bread. It’s a place to get food and drink and, attached to the bar, is the mothership for the best-ever breads. Lots to sample, sweet and savory. I usually bring many loaves home but – since covid – have ordered my favs. In 2020, when I couldn’t vacation in Maine, one of my friends (who owns property nearby) brought bread back for me. But I missed it so much that I had a bunch of loaves sent to me.
  • Ogunquit has awesome scenery. You can grab a bite to eat here during the day and then take the walking path, which meanders along a hill overlooking the ocean – and worth the walk. Also look for Perkins Cove because it is a romantic little place with stores and cafes – small but nice. I can recommend 2 good restaurants: Pizza Napoli, owned by my friends, Robert and Michael, and Roberto’s – where they hang out when not at their own place.
  • Kennebunkport is a quiet town which boasts the Bush compound – which you can only see from a distance
  • Old Orchard Beach may be the most popular family town for summer visitors. It reminded me of Ocean City NJ – and a bit too busy for me. However, if you want a lot of family-friendly activity, it could be your favorite place.

Portland/Casco Bay

  • About an hour north of Kittery and Ogunquit is Portland. This town is a great overnight and even worth a few days. Portland is a major city – but not like Philly and much smaller and very walkable. When I first went to Portland, much of the downtown (Old Port) was a burned-out place, and a little scary. Not anymore. By 2019 it was all small shops and cool bars – and The Holy Donut – another foody place not to be missed. Amazing potato donuts (I don’t much care for either donuts or potatoes, but these potato donuts are dream-worthy!)
    • Where to Stay
      • Uptown – Congress Street is the main drag for traditional stores and there’s lots of activity. I’ve stayed at the Westin and my favorite thing is watching the sunset and having drinks at the rooftop bar. I also loved the small eateries up, down, and around Congress Street.
      • Old Port – I’ve also stayed downtown by the waterfront, e.g. at a Marriott. Both the area and the hotel are just OK – and, I think, a lot more expensive; I like uptown better for its location.
      • Scarborough is just outside of the city and an easy drive into Portland. It has several chain hotels, and less expensive in cash/easier to  exchange points during high season. However, make your reservation early to get your best deal.
    • What To Do
      • There are many things to do in Portland and, during  the summer months, lots of events. So check local listings and the local Patch to find them. Here are some good standards that, if you are only doing an overnight or weekend, your best bets:
        • Portland Art Museum there – decent but not someplace I would visit again.
        • The Victoria Manson is a historical house that was slated for demolition and saved by a history-focused group. It’s been lovingly restored. I’ve seen a couple times – worth it if you like that kind of thing.
        • Portland Headlight is one big place not to be missed. It’s a beautiful lighthouse in a peaceful coastal setting – and the park is a good place to walk, see the sites, take pix, and suck in some of that good Main salt air.
        • Becky’s Diner on Commercial Street is THE place for breakfast. You’re likely to wait 30-60 minutes to get in, but it’s good diner food and real Maine atmosphere…and at an average price.
        • The Holy Donut has a couple locations and, even though I don’t care much for potatoes or donuts, I crave these!
        • The Portland Observatory is on the northern end of the peninsula. It’s a civil engineering feat and the the last historic maritime signal station. It’s a great stop if you have a couple hours. If you time is right, you can visit here and then get something to eat in Munjoy Hill.
        • Walk! During the day, consider walking around the city of Portland. It has several funky neighborhoods that are interesting to observe on foot. I like seeing very old buildings on Congress Street. Also, the intersection of Congress, Free, and High Streets is a bustling place – and, at night – is an amazingly cool visual treat.
        • Enjoy the vibrant Night Life. There are lots of cool places but they turn over fast, so check Yelp or Trip Advisor to see what’s
    • Most of the restaurants have average offerings, but good ones. There are some interesting upscale places in Munjoy Hill section on the northeast section of the peninsula.
    • The Trader Joe’s in Portland carries a large selection of locally brewed beers. Rising Tide is Joseph’s favorite (Portland-made) beer, but he likes to try others too.

Leaving Portland, going north – on the highway I295 – you can stop in Freeport, Home of LL Bean. If you’re a fan, you can get some discounts there. There are some cute shops and also a small When Pigs Fly bread store and a Ben and Jerry’s Ice Cream. However, unless you have a purpose for going, it’s not a “must do” stop.

If you want to drive straight through from Portland to Bar Harbor, you can take I295 north toward Augusta and then pick up I95 at Gardiner into Bangor (where Stephen Kind lives) before going east to Bar Harbor. That drive is about 3 hours.

OR, if you want to meander up in coast, you can take I295 out of Portland and get onto scenic Rt. 1, which takes you through the small towns. I like doing that on the way to Bar Harbor, through tiny towns on Rts 1 and 3, in the way into Ellsworth – the county seat and the city closest to Bar Harbor (and where all the regular grocery stores, Walmart, etc. are). Personally I like doing it on the way up but, on the way back (and because I’m ready to get home) Joseph and I go the more direct route, driving west from Bar Harbor to Bangor and then south on I95 out of Maine.

IF YOU GO SCENIC RT 1: There are lots of little towns along the way – some more interesting than others – but each one having its own special charm. Here are some I’ve been to and visit from time to time:

  • Wiscasset: Off the beaten path, is Wiscasset – home of Red’s Eat – internationally lauded for its lobster rolls. It’s literally a shack in the center of town. Expect to wait in line about an hour to order at the window and another 20” from the time you order until you get your food. If you go between lunch and dinner (around 2-3pm) it’s faster – hardly a line. Either way, if you love lobster roll, it’s the best around. FYI: if you’re with someone who isn’t a fish person…Joseph doesn’t eat it and gets a sirloin steak sandwich.  Both are wicked good!
    • Don’t let the time in line stop you. If you’re friendly, you’re likely to meet some interesting people and have some cool conversations. However, it’s sunny – so wear your hat to guard from too much sun.
  • Boothbay Harbor – about 20 minutes from Wiscasset, this is a quaint coastal town of lighthouses and the longest wooden footbridge in the country. It’s also where the old-time musical Carousel was filmed
  • Monhegan Island: Between Freeport and Wiscasset, and off the coast, is Monhegan Island. This is a magical place where several of the Wyeth family own or have owned houses there. I believe Jaime still do and still paints there. You have to plan this trip in advance – and it makes sense to stay at a B&B overnight – because you can only get to the island by mail ferry, leaving from Port Clyde at 7am, and you return the same way in late afternoon.
    • It’s an adventure if you go, and worth the extra effort. Don’t forget to visit the iconic Port Clyde Lighthouse.
  • Damariscotta: Just past Wiscasset is Damariscotta. This little town is worth stopping in for a short stay…because it’s sooooo Maine. And it’s the home of the original RENY’s – the funky department store you see all over Maine.
  • If you are staying on the coastal road, you’ll practically run right into Rockland, Rockport, and Camden.
    • Rockland is a sweet little town and home to the Rockland Breakwater Lighthouse (which you can only get to by foot – 3/4 mile one way) and the Farnsworth Art Museum, which houses both local artists and many famous Wyeth family paintings.
    • Just north of Rockland is Rockport, a beautiful harbor town.
    • Same with Camden jut up the road – “jewel of the coast” – with lots of big boats and yachts. You could visit both of those in a day. And, while in Camden, you could go to Camden Hills State Park and take a hike up Mount Battie for some ama zing views of Penobscot Bay.
  • Continuing north you’ll pass through towns like Belfast, Stonington, Deer Isle, and Blue Hill.
    • Blue Hill is called the considered the gateway to Acadia. If you read Charlotte’s Web as a kid…Blue Hill was the home of EB white, who wrote Charlotte’s web. If you go there around Labor Day, you can go to the Blue Hill Fair – and don’t be surprised if you feel like you just walked into Charlotte’s Web…because you are! White fashioned the county fair in his book after the Blue Hill Fair. I didn’t know that when I went to the fair the first time. Still, I noticed how much it reminded me of the book. It was a year or two later that I learned it was White’s hometown – that’s how good his descriptive writing was!
      • If you go to the fair, you’re very likely to see Wilbur there – though Charlotte sees to stay out of site whenever I’ve gone.
  • As you get closer to Bar Harbor, you’ll pass through Bucksport.  This is the place that boasts (what I think) is the scariest bridge ever: The Penobscot Narrows Bridge – one of only 3 such bridges in the country. I don’t drive over it – I drove over the rickety old one, but this one is too much for me. Fortunately it doesn’t bother Joseph. However, there are two things you can enjoy around here:
    • Penobscot Narrows Observatory: This is the tallest bridge observatory in the world. Visitors can go inside the observatory and to the top – and it’s very cool to be there and see the river and adjoining town from almost (I think) a half-mile up.
    • On the same side of the river as the observatory is Fort Knox – and interesting military compound leftover from the Civil War. It’s worth seeing once – and it isn’t very expensive to visit.
    • Just over the bridge is Verona Island – a good place to stop and have a picnic by the Penobscot River.
  • About another half-hour drive and you are in the town of Ellsworth – the county seat and the town that serves Mt. Desert Island.
    • There’s a lot of history here, including the Woodlawn Museum, once owned by wealthy captain who created much of Ellsworth’s trade one hundred or more years ago, and the Ellsworth Bird Sanctuary.
    • Ellsworth features a lot of entrepreneurs, artists, and a few restaurants. My go-to is the Riverside Café but I’ve also enjoyed dinner at the Irish bar (Finn’s Irish Pub). Joseph loves visiting the British me-too pub (Airline Brewing Company). The first time we went they didn’t serve more that picky snacks, but now they have a menu – including bangers and mash and even pasties. Being there is like being in the UK.
    • Ellsworth is also where the main grocery shopping is with a few major grocery stores and Walmart are.

Bar Harbor is east of Ellsworth. BUT, if you go north from Ellsworth, you’ll pass the Schoodic Peninsula and be heading toward Canada – and how you travel if you want to hike Mount Katahdin. I’ve never done it, but I have explored the little towns along the way, including the Quoddy Lighthouse and Campobello, former summer home of FDR.

From Ellsworth, drive about 30” onto Mt. Desert Island. There are 3 main harbors on Mt. Desert:

  • Bar Harbor, touristy but quaint with the largest number of stores and restaurants
  • Southwest Harbor, small and with a slightly upper middle-class vibe
  • Northeast Harbor, where you’ll see the yachts and could even run into a Rockefeller, Dick Wolf, or Martha Stewart.
  • There are other, smaller places, like Pretty Marsh, but unless you know someone there or have something to do there, it’s not a good use of time – but it’s also where some of the best seasonal restaurants can be found. It’s hard to say which ones because those island restaurants can be gangbusters one summer and gone the next.

The primary thing on Mt. Desert is the spectacular Acadia National Park. It’s filled with breathtaking beauty, and more hikes than you can imagine, as well as carriage trails that go through the prettiest parts of the park.

  • Start at the Visitor center and get a park pass. You may have to make a reservation to get into the park – and the rangers will tell you.
  • Drive the Ocean Drive to get a feel for the park. You’ll drive through or past places like Thunder Hole.  You can get out and walk a little bit or a lot.
  • Plan to go up to Cadillac Mountain, the highest peak – and the first place the sun comes up on the east coast.
    • You can hike up the mountain and I’ve done it a couple times – and that’s fun. It’s more fun to hike up the mountain and walk back on the road (but be careful).
    • Drive up the mountain for either sunrise or sunset – two of the best things to do in Acadia.
      • When you go for sunset, go early. Lots of people go, so it gets crowded. One year there was someone who got freaked out by the height and drove about 5mph, and we missed the sunset
      • Once I took friends, who was visiting for the day, up to Cadillac and there was a man on the mountain playing bagpipes…it was amazing!
  • Many of the hikes start of the Jordan Pond House, so it’s hub and gets busy. Get there early for parking. Two good hikes from that hub are the
    • Jordan Pond Path (goes around the pond – takes about 2 hours). Half the path is a flat path and the other is through the woods and over boulders – dress with appropriate foot gear. From Jordan Pond House, I like starting on the left side because it’s the more challenging part. Halfway around, at the base of “The Bubbles” the path flattens out.
    • Jordan Stream Path
      • This is the opposite direction from the Pond and through the woods to Seal Harbor. The return in on a lovely carriage road
    • Popovers at Jordan Pond House are a must – out in the backyard looking at The Bubbles – a good way to end either hike
  • Two other favorite hike are:
    • Ocean Path, which starts  at Sand Beach and is relatively easy – no big boulders to climb over – with amazing views all along. I like doing this one in late afternoon because that’s when it’s the least crowded. I bring a snack to eat at the end of the way out while enjoying the lowering sun. The way back to Sand Beach is during sunset and the changing colors makes the trek even better.
    • Connors Nubble, not as easy one going up the mountain – but not real strenuous. Then, when you come down the mountain, you end up on a flat carriage trail.

Night Life: Don’t expect a lot of nightlife in Bar Harbor. But if you hike all day, that might not matter. If I finish a hike in the latter part of the day, I enjoy having a drink at happy hour in one of the many outdoor bars. The restaurants are good. I like Havana, Café This Way, Jeannie’s Great Maine Breakfast and the Black Friar.

Where to stay: I stay at Windward Cottages – and they are the best! They are housekeeping cottages overlooking Clarks Cove. Owner Ollie Wenger does everything to make sure you have a good stay. Also, I like that all the harbors are about 15” from the cottage. And some of the good eating places are outside of Bar harbor areas…like Mothers Kitchen for lunches (across the street from the cottage), Burning Tree, The Common Good (popovers) and Red Sky (Southwest), Beal’s Lobster Pound, and XYZ.

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What are the Maine Diaries?

The Maine Diaries is a fun look at my annual adventure to New England where I unwind from normal life and reconnect with myself.

I was captivated by the Maine Coast on my first trip there in the late 90’s. In the years since, I’ve traveled up and down the coast from Kittery to Calais but I spend most of my Maine time Downeast. I love the adventures I have and the chance to unwind from the world and restore my inner clarity. I chronicle my experiences in The Maine Diaries.

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Maine Diaries

Every year Annmarie Kelly embarks on a trip to Maine where she reflects on her life, the years challenges and successes while seeking solace and adventure in the beautiful Northeast wilderness.

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