Indianapolis in 2 Days for Friends - Brunch at the acclaimed Milktooth
A fun, vibrant 2-day plan for a group of friends who love good food, live music, playful activities, and easy shared costs. Designed for September (pleasant autumn weather) with walkable neighborhoods, a self-guided bike ride on the Cultural Trail, an escape room, food-hall lunches, and evening live-music options.
Highlights
- Brunch at the acclaimed Milktooth
- Self-guided Cultural Trail bike ride via Pacers Bikeshare
- Food-hall lunch at Indianapolis City Market
- Escape room challenge with Breakout Games
- St. Elmo Steak House dinner and spicy shrimp cocktail
- Afternoon at Newfields (outdoor art + gardens)
- Broad Ripple nightlife and live music at The Vogue
Itinerary
Day 1
Arrive ready to explore: brunch, the artsy Mass Ave, a food-hall lunch, a Cultural Trail bike ride, canalside relaxing, and a marquee dinner + live music to close the night.
Brunch at Milktooth (Fountain Square)
Start with inventive brunch plates and shareable dishes — perfect for groups that want to try a few things.
Tips from local experts:
- Milktooth is popular — arrive at opening or expect a line; put your name in early via their host desk for faster seating.
- Order a few shared plates to sample menu highlights (good for splitting costs and trying more items).
- September mornings are mild; the neighborhood patio fills quickly — ask for a patio table if you want people-watching.
Stroll Massachusetts Avenue (Mass Ave) — shops & murals
Walk off brunch exploring indie shops, street art, galleries and boutique stores on Mass Ave — a lively stretch with bars and photo ops.
Tips from local experts:
- Metered street parking is common; have ParkMobile or similar app ready for quick group drop-offs.
- Pop into a few art galleries and boutique shops that allow quick purchases and are group-friendly.
- Mass Ave has lots of murals — plan a few quick photo stops (great for social media) and set a meet-up point if people split up.
Lunch at Indianapolis City Market (food hall)
Choose from multiple vendors under one roof — easy for groups with varied tastes and for splitting checks at different stalls.
Tips from local experts:
- Sit at communal tables to keep the group together — it’s the easiest way to try multiple vendors.
- Bring small bills for quick vendor purchases; many vendors accept cards but having cash speeds things up.
- September usually has open windows and a pleasant breeze in the market — try local specialties and grab snacks for later.
Pacers Bikeshare + Cultural Trail: Self-guided bike loop
Rent bikes via Pacers Bikeshare for a lively group ride on the Indianapolis Cultural Trail — scenic, active, and social.
Tips from local experts:
- Download the Pacers Bikeshare app in advance and have a valid card/ID handy — docks are plentiful along the Cultural Trail.
- Plan a 60–90 minute loop with quick photo stops (Monument Circle, canals, public art) — helmets are recommended for group rides.
- September evenings can cool quickly; bring a light layer for after the ride and stash it in a small backpack or dock lockers if possible.
White River State Park & Canal Walk — easy riverside stroll
Wind down with a canal-side walk through White River State Park, take photos and relax near the water and green spaces.
Tips from local experts:
- The Canal Walk has plenty of benches and photo-friendly spots — pick a sunny stretch for golden-hour photos in September.
- If your group wants more activity, bring or rent light water gear nearby; otherwise, enjoy a picnic-style snack from the City Market.
- Watch for event setups in September (concerts/festivals): they add energy but can change parking; leave extra time if traveling onward.
Check in / Break at Omni Severin Hotel
Freshen up and relax before dinner — ideal mid-evening regroup for everyone to recharge and change.
Tips from local experts:
- If you’re not staying here, Omni Severin is a convenient downtown spot to use as a meetup/refresh location — call ahead if you need to store bags.
- Ask the front desk about nearby valet or short-term parking options if anyone has a car (splitting valet between the group reduces per-person cost).
- Evenings in September cool down — use this time to swap to a light jacket for later outdoor walks between venues.
Dinner at St. Elmo Steak House (classic Indy dining)
A landmark dinner spot — shareable steaks and the famous spicy shrimp cocktail; great for a memorable group meal.
Tips from local experts:
- Reservations are strongly recommended for groups — request a table for 4–6+ and ask about separate checks up front if needed.
- Don’t miss the spicy shrimp cocktail — a classic Indy specialty; consider ordering one per two people to share.
- St. Elmo is cozy; for larger, louder groups ask host for a corner table or private alcove to keep the vibe lively and contained.
Live music & late-night fun at Howl at the Moon
Finish the night with energetic live piano-driven shows and a DJ — ideal for groups who want to sing along and dance.
Tips from local experts:
- Expect a cover charge on busy weekend nights; buy tickets early for special events and reserve a table if available for your group size.
- Howl at the Moon is very social — pick a central table for easy mingling and rotating group members onto the dance floor.
- Late-September nights can be refreshing outside — step out between sets for quick fresh-air breaks and downtown skyline photos.
Day 2
A playful second day: chef-driven brunch, an escape-room challenge, pizza for a casual lunch, cultural time at Newfields, and Broad Ripple nightlife to close out the weekend.
Brunch at Bluebeard (Fletcher Place)
Chef-driven brunch in a cozy, stylish spot — great for a relaxed start with shareable plates and craft coffee.
Tips from local experts:
- Bluebeard accepts reservations for larger groups — reserve a table to avoid waits for a party of friends.
- Try to split a couple of entrees family-style; portions are generous and good for sharing to keep costs down.
- September patio seating is pleasant — request outdoor seating if you want that neighborhood vibe before heading out.
Escape room challenge at Breakout Games Indianapolis
Work together solving puzzles and racing the clock — an energetic group activity that’s great for friends.
Tips from local experts:
- Book a private room for your group size (4–6 is ideal) so you have the full experience and don’t mix with strangers.
- Arrive 15 minutes early to get a quick briefing and store bags/phones in provided lockers.
- Choose a room difficulty that suits your group (moderate for mixed puzzle experience) so everyone stays engaged and it's fun, not frustrating.
Casual lunch at Bazbeaux Pizza (Mass Ave)
Big, shareable pizzas perfect for groups — easy to split bills and linger if you want to chat.
Tips from local experts:
- Order a couple of different pies and let everyone grab slices — Bazbeaux is designed for sharing and group dining.
- Ask for separate checks at the start if the staff can accommodate, or use one bill and Venmo to split easily.
- September patio seating is comfortable — request outdoor seating to enjoy Mass Ave ambiance between bites.
Newfields (Indianapolis Museum of Art) — gardens & outdoor art
Roam the galleries and expansive gardens — a relaxed cultural stop with beautiful outdoor sculptures and lawns.
Tips from local experts:
- Buy timed-entry tickets in advance for weekend visits to skip lines; the campus is large so allow time for walking between exhibits.
- Bring a light sweater for cooler September afternoons and plan to sit on the Great Lawn for photos and group downtime.
- Check for special seasonal exhibits or evening events in September (often music or cocktail nights) that can be fun for a group.
Explore Broad Ripple Village — breweries & local shops
Head north to Broad Ripple for craft breweries, street murals, and a lively neighborhood perfect for bar hopping.
Tips from local experts:
- Broad Ripple has concentrated bars and breweries — pick 2–3 favorites and do a short walking route to keep the night moving.
- Use rideshares between distant stops if your group plans to sample alcoholic flights to avoid parking stress.
- Watch for live bands and open-mic nights in September — many venues are group-friendly and accept walk-ins early evening.
Dinner & live show at The Vogue (Broad Ripple)
Catch a concert or live set at a classic Broad Ripple venue — dinner nearby and then a show for a lively finish.
Tips from local experts:
- Check The Vogue’s event calendar and buy tickets in advance — popular shows sell out, especially on weekend nights.
- Reserve a dinner table at a nearby restaurant if you want a pre-show meal; many Broad Ripple spots handle groups and split checks easily.
- If driving, use nearby public lots or rideshare; street parking fills fast on event nights — plan 20–30 extra minutes for parking.
Optional late-night drink: neighborhood bar in Broad Ripple
Keep the night going at a lively bar — perfect for a final round, recap, and planning your next Indy trip.
Tips from local experts:
- Ask the bartender about local craft brews or a shared pitcher to keep costs manageable for a group.
- Many Broad Ripple bars accept cards and offer tabs; confirm how the tab will be split to avoid awkwardness later.
- September nights are crisp — pick a spot with a small outdoor area to enjoy the evening breeze between sets.
Itinerary Attributes
| Days | 2 |
| Highlights | 7 |
| Season | - |
| Month | - |
| Persona | Friends |
| Transfers | - |
| Restaurants | 5 |
| Total Activities | 15 |
| Total Places | 15 |
| Activities Types | Meal, Neighborhood, Experience, Outdoor, Hotel, Restaurant, Nightlife, Culture |
