Portland, ME is a Pajama Jean kind of town. It’s a Pajama Jean town, because it’s a bakery town, a specialty food town, a fine dining town, a fresh produce town and a bagel town. You get the idea. It’s a place where you wonder who makes you more angry: that guy who just got the last Sicilian slab at Micucci Grocery or the sadistic jerk who decided to fasten pants with buttons and zippers. Either way, a weekend in Portland is always bound to be a delicious journey. Although my mom and I planned our girls’ weekend around our Fore Street reservation, some of our most memorable bites were enjoyed in-between meals.

Whoopie Pies at Two Fat Cats Bakery

I’ve mentioned before that the whoopie Pie has never been my confection of choice, but my mom has always wanted to try one from Two Fat Cats. While the pastries in the small bakery case looked a little anemic, gorgeous pies – real pies, that is – caught my eye with their rustic, golden brown crusts and vibrant fruit filings. Luckily for our arteries, those were only sold whole, and we left with two moderately sized whoopies.

These weren’t those burger-sized, flying orbs from space that you often see. I have to hand it to Two Fat Cats; their classic chocolate whoopie pie really was classic. It achieved that light chocolate flavor in the fluffy but slim-as-a-pancake cake without tasting artificial. It was held together with a marshmallow filling made with the real thing: seven minute frosting, not some questionable “marshmallow crème.” The seasonal pumpkin whoopie was a little more dense but had a nice fall flavor without being overwhelmingly spiced. Here, the seven minute frosting was subbed for a ligther-than-air maple buttercream that seemed too overtly maple for me.

Housemade Chocolates from Fore Street

The dessert menu at Fore Street features a selection of chocolates, which you can have plated or boxed to take home. Some of the chocolates we received, though, did not match their menu descriptions. The sesame truffles were perfect: dark, rich and creamy with an earthy, nutty flavor. The advertised “white chocolate bark with pepitas” turned out to be a thin, inch-long slab of white chocolate peppered too heavily with pumpkin pie spices and filled with chopped pecans. The “peanut crunch” was apparently replaced by a thin piece of milk chocolate studded with plump dried cherries and sparse shards of caramelized sugar. Espresso bonbons were filled with a thick dark chocolate ganache.

where the magic happens. after hours.

Breakfast Pastries from Standard Baking Company

Excuse the pun, but the bread and pastries here really represent the standard by which all others should be judged. My mom and I woke up early to grab breakfast Sunday morning and brought the goods back to the hotel for fear that the morning pastries would rightfully be sold out if we went at our leisure. The morning bun should not be confused with a sticky bun. Its base is buttery but not heavy and almost flaky. Swirls of cinnamon sugar glaze set up like a lacquer in spots but stay moist in others. I love it because it’s not overwhelmingly sweet, but that doesn’t mean I don’t know that the best bite is that bit at the bottom of the roll which catches all that caramel that seeped through while warm.

The gingerbread was a surprising treat. The pure molasses and ginger flavor was intense and not muddled by the addition of lots of other spices. The round of cake was weighty and very moist. Its winter warmth was brightened by a paper-thin coating of a glaze perked up with some lemon.

Truffles from Dean’s Sweets

Dean’s Sweets resides next to Rabelais, which I previously deemed “the best store in the world.” When faced with a case full of jewel-like truffles, we chose four (these guys were expensive!) that we thought characterized Maine: The Needham, the maple, the blueberry, and the milk chocolate sea salt caramel. Aw, aren’t we cute (or hokey)? The caramel-filled truffle with Maine sea salt was a favorite of mine, because its chewy caramel was nearly black, and I wax poetic over burnt caramel. The bitter caramel was tamed by the sweet milk chocolate coating.

Lunch at 158 Pickett Street Café

Initially, I wanted to do a bagel crawl while in Portland but a lack of the aforementioned Pajama Jeans or other stretchy pants of the like prevented that from happening. Now bagels in Maine aren’t exactly like Montreal bagels, but they are more akin to their Canadian counterparts than to the NY style bagel. This quirky little shack of a restaurant served up a toasted bagel that was almost (almost) light and more like a fine bread. It was chewy with a hole structure to it. The outside was perfectly crisp and golden and really contrasted in texture with the slightly sour innards. We had it smeared with a luxurious herbed cream cheese, filled with the appropriate amount of roughly chopped and verdant green fresh parsley, dill and scallions.

Our other dish was a simple but somehow extraordinary tuna salad, which I am definitely going to recreate. Pearly white canned albacore tuna was tossed with the slightest bit of mayo, small chopped romaine lettuce, capers, chopped pickles, thin slices of cucumber and red onion, and fresh dill. The dressing was light and mildly sweet, with a bit of Old Bay seasoning. My guess is that the secret behind the salad’s success was the incorporation of some of the tuna water. Don’t balk. I know this might sound like a mess, but it was refreshing and flavorful mess. We brought home another plain bagel with a side of an overly vegetal pumpkin cream cheese and an aromatic garlic bagel.

Rosemont Market & Bakery

Rosemont Market is a small neighborhood grocer for in-the-know locals. This became immediately apparent when I opened up a cute cupboard that housed freshly baked pastries and took a looksie to find out which treats we shoud try. My mom and I split a rugala (who knew there was a singular form of rugelach?) on the ride home and almost had to pull over. The soft, tangy cream cheese dough was rolled thinner than is traditional and coiled several times around a simple filling of cinnamon and ground nuts. The crisp sugar coating provided a great contrast to the soft chewy dough that flaked away with every bite. We also managed to score some delicious locally grown produce, including a really sweet russet apple.

After rolling out of Portland two weeks ago, I’ve been terribly sick, so the feast was justified. I had to bulk up in preparation for weeks of eating only yogurt, applesauce and broth (and, sadly, no turkey).