*This is part of a series called A Nanny’s Guide, for more posts click Here*
Here at The Teaching Nanny we’re all about encouraging Nannies to perform at their absolute best. One of the ways of becoming a rock star nanny is knowing all the fun kid friendly places in your city! Since nannies hold the pulse on their neighborhoods, we thought it would be fun to highlight those activities in a few major cities this summer! Coming up we have Chicago! If you live in a major metro area in the US and would like to be featured, please fill out this form here, we’d love to hear from you!

If you’ve been around the nanny Instagram community for a little while, you’ve probably come across Emma from @themainenanny. She’s such a light in the nanny world! Her guide to Portland, Maine is broken down into Restaurants, Nature, Beaches, Parks, Playgrounds, and Excursions! Make sure you read all the way to the end for fun pictures!
Restaurants
Miss Portland Diner
– High chairs are available, but be warned that this is a super popular spot! Wait times can get long in the summer months (especially on the weekends). If you have older kids or little ones who can sit on a lap, try getting a seat up in the original diner car (it’s all booths up there, so not highchair friendly but oh so fun)! CLOSED on Wednesdays! I highly recommend their pancakes; they’re the size of the plate and come with real Maine maple syrup; to die for!
Standard Baking Co.
– Do yourself a favor and swing by Standard, located right off of Commercial street in the Old Port. Hands down the best bakery/bread shop in Portland! Perfect stop for some bread to go with dinner or for a sweet treat to start off your day (the pain au chocolate’s are MY FAV)!
Otto’s Pizza
– With 5 locations throughout Portland, this place is legendary- and it entirely lives up to the hype! Delicious thin-crust pizzas made with the best sauce you’ll ever eat. They have all the classic flavors and a bunch of amazing unique ones too (mashed potato, bacon, & scallion is a favorite of mine)!
The Great Lost Bear
– A Portland staple! Great stop for any beer loving parents/Nannies (not on the clock, of course), as they have over 70 on tap! Great kids menu too!
Salvage BBQ
– Absolutely delish and super kid friendly!
Highroller Lobster Co.
– The perfect spot to go if you’re wanting to have a classic Maine lobster roll experience!
Green Elephant
– Great vegetarian spot with tons of delicious options!
Nature
Baxter Woods
– Trails easily navigated by foot and jogging stroller friendly! Located in the North Deering side of town, there’s picnic tables at the opening and tons of wooded trails to explore!
Beaches
– There’s so many great spots but here are some of my nearby favorites:
– Pine Point in Scarborough (free parking)! Classic sandy beach.
– Willard Beach in South Portland (fun sand bars at low tide)!
– East End Beach (all rocky, no sand). That part of the coastline is a deep water mooring (AKA, not tidal, meaning the beach is there pretty much 24/7!)
Parks
Deering Oaks Park
– A great place to walk, see the ducks, have a picnic, go ice skating in the winter, watch a ball game in the summer and of course a great playground to play on. In the summer there is a fun wading pool and fountains.
Baxter Boulevard
– Amazing walking trail around Portland’s Back Cove. Children love to walk, run, and play on the park course apparatus. Good place to ride bikes too. Adjacent to Payson Park!
Fort William’s Park
– No trip to Maine would be complete without seeing a lighthouse! The Portland Head lighthouse is truly iconic, and the views of Casco Bay are stunning. If you’re lucky, you might see some sunning seals or breaching whales!
Evergreen Cemetery
– I know, I know. Cemetery? Just trust me on this one. Beautifully landscaped and sprawling, absolutely perfect to go for a walk and let your kiddos run/walk/skip a bit ahead of you without fear of traffic.
Friends of Deering Oaks Park
-Our new favorite playground! Nestled in a green oasis right in the middle of the city, the playground has something for kids of all ages. In the summer months, kiddos can play with the water pump feature (our favorite). With 55- acres, there’s plenty to see and do. Take a stroll to the duck pond (there’s even a little house in the middle), cool down in the splash pad (in the summer months), play tennis, basketball, or volleyball. Have a picnic, etc.! Note of wisdom from a local: Unfortunately, Deering Oaks is only a few blocks away from Portland’s homeless shelter. The playground is set far enough back that it’s not usually an issue there, but use a healthy does of awareness and caution if you go wandering around the park at large.
Playgrounds
Eastern Promenade Park and Children’s Playground
– Easily my favorite local playground! Why not enjoy a stunning view while you play? (We’re talking STUNNING waterfront views: sailboats, kayakers, and even historic Fort Allen in the middle of the bay). This playground has copious amounts of easy street parking, and is stroller friendly (located on a expansive hill, but there’s a gravel stroller ramp just to the left of the playground)! In the warmer months, you can grab a bite to eat at one of the many food trucks and enjoy a picnic after you play! Just a few minutes walk down the hill you can find the Eastern Promenade Beach (perfect to stroll along and hunt for seashells), the Narrow Gauge Train, and the Back Bay walking/cycling path.
Payson Park Playground
– This playground is great, especially if you’re juggling multiple kids, because it’s entirely fenced in! If open fields, tennis, basketball, or baseball are more your speed: fear not, Payson Park has it all, (including views of beautiful Back Bay)! Plenty of parking nearby & stroller friendly path.
Heseltine Park
– Located on Irving Street, at the intersection of Ocean Ave. Nestled in a quiet residential neighborhood with lots of old growth trees overhead for shade, it’s usually quiet and peaceful. Even has a smaller structure that’s great for little ones!
The Point at Eastpoint Christian Church
– Be sure to check out their social media for up to date hours, but you can expect The Point to be open traditional hours throughout the week! My home church, Eastpoint, has a beautiful facility that’s open to the public and the perfect place to escape heat, rain, or snow. Climate controlled (yes, it has A/C in the summer months, thank God) there’s a standard size soccer field of indoor turf PERFECT for running around, kicking a ball around, and getting those wiggles out! PLUS- there’s a full PlayScape! Kick off your kiddo’s shoes and let them run wild through the full-sized (think: McDonald’s PlayPlace but better) playscape, and there’s even a smaller section for littler bodies too! *Spacious bathrooms easily accessible!
Excursions
Children’s Museum & Theater of Maine
– BRAND NEW and beautiful facility located out by Thompson’s Point boasts easy parking and waterfront views. Restrooms on all 3 floors! Highly recommend everything on the 3rd floor: aquarium, light exhibit & water/ball areas!
Peaks Island Ferry
– Casco Bay Ferry Line- round trip tickets start at $7.70 for adults & kids under 5 ride free. Take a quick and easy half or full day trip out to Peaks Island (only 17 minutes on the ferry each way). Head up the hill for one of Lisa’s famous cinnamon buns at the Peaks Café, grab lunch at one of the 3 island restaurants, or enjoy an ice cream from Down Front. Older kids would enjoy exploring on foot, bike, or kayak (easy rentals from Brad’s Island Bike and Maine Island Kayak).
Narrow Gauge Railroad
– Located right between the Old Port and the East End, this museum offers train rides year round. Beautiful views (it’s right on the water) and so fun! The themed and seasonal rides (including Ice Cream Train and Polar Express) are extra special if you’re in town at the right time.
Lucky Catch Cruises
– Older kids will love this one! Lucky Catch’s lobster boat will provide an unforgettable excursion on the waters of Casco Bay while they guide you through the daily routines of a Maine Lobsterman. (Plus you can eat a genuine Maine lobster afterwards)!
Down East Duck Adventures
– The wow factor of a duck boat ride is UNREAL! Climb aboard as they twist n’ turn through the historic city of Portland and without skipping a beat, they splash into beautiful Casco Bay.
Bayside Bowl
– Located in Downtown Portland, Bayside Bowl is kid friendly bowling (with the option of lane bumpers) and full service restaurant. Also great for grownups 😉 In the summer months they have a fun rooftop bar and delicious tacos!
Wolfe’s Neck Farm (in Freeport/15 min from Portland).
-They have a livestock barn with baby cows, goats, and sheep that you can meet and pet! The land there is plentiful and beautiful too! There’s a tiny little rocky beach and acres of fields to run around!
LL Bean (in Freeport).
-Take a picture in front of the iconic Bean Boot! Fun place to walk around with kids, especially on a rainy or snowy day. The hunting and fishing side is great- tons of super cool taxidermy wildlife (including deer and a giant bear). They have the famous Locked Moose exhibit too: it’s two moose who got antler locked and died that way! They have a great kids area too.
Maine Wildlife Refuge (in Gray).
-All the animals are unfit to be in the wild (whether by human dependence or injury). It’s like the zoo, except all wildlife animals and guilt-free! See cool critters like deer, owls, peacocks, foxes, cougars, and even a MOOSE!
Thank you so much for sharing Portland with us Emma! Make sure you give her a follow on Instagram @themainenanny She’s always on some sort of fun adventure!








